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Synthesis 2013; 45(17): 2343-2371
DOI: 10.1055/s-0033-1338501
DOI: 10.1055/s-0033-1338501
review
Metalated Indoles, Indazoles, Benzimidazoles, and Azaindoles and Their Synthetic Applications
Further Information
Publication History
Received: 30 April 2013
Accepted: 02 May 2013
Publication Date:
15 August 2013 (online)
Dedicated to Victor Snieckus on the occasion of his 76th birthday
Abstract
This review focuses on the regioselective metalation of condensed azoles, such as indole, indazole, benzimidazole, 4-, 5-, 6-, and 7-azaindole. The metalation strategies discussed include halogen–metal exchange, metal insertion into carbon–halogen bonds, and directed deprotonation. The influence of different nitrogen-protecting groups and directed metalating groups is discussed. This review covers literature published mainly from 1991 to 2010.
1 Introduction
2 Metalation of Indoles
2.1 C2-Metalation of Indoles
2.2 C3-Metalation of Indoles
2.3 C4–C7-Metalation of Indoles
3 Metalation of Indazoles
4 Metalation of Benzimidazoles
5 Metalation of Azaindoles
6 Conclusion
-
References
- 1a Pozharskii AF, Soldatenkov AT, Katritzky AR In Heterocycles in Life and Society. Wiley-VCH; Weinheim: 1997
- 1b Ardeo A, Collado MI, Osante I, Ruiz J, Sotomayor N, Lete E. Targets Heterocycl. Syst. 2001; 5: 393
- 1c Charushin VN, Chupakhin ON. Pure Appl. Chem. 2004; 76: 1621
- 1d Kirsch G, Hesse S, Comel A. Curr. Org. Synth. 2004; 1: 47
- 2a Gschward HW, Rodriguez HR. Org. React. 1979; 26: 1
- 2b Snieckus V. Chem. Rev. 1990; 90: 879
- 2c Marek I. Chem. Rev. 2000; 100: 2887
- 2d Knochel P, Millot PJ, Rodriguez AL, Tucker CE. Org. React. 2001; 58: 417
- 2e Schlosser M. Eur. J. Org. Chem. 2001; 3975
- 2f Hartung CG, Snieckus V In Modern Arene Chemistry . Astruc D. Wiley-VCH; Weinheim: 2002
- 2g Schlosser M. Organometallics in Synthesis: A Manual. 2nd ed.; Schlosser M. Wiley; New York: 2002: 1
- 2h Marek I. Tetrahedron 2002; 58: 9463
- 2i Clayden J In Selectivity for Synthesis . Baldwin JE, Williams RM. Pergamon/Elsevier Science Ltd; Amsterdam: 2002
- 2j Leroux F, Schlosser M, Zohar E, Marek I In Chemistry of Organolithium Compounds . Rappoport Z, Marek I. Wiley; New York: 2004. Chapt. 1, 4
- 2k Leroux F, Jeschke P, Schlosser M. Chem. Rev. 2005; 105: 827
- 2l Schlosser M. Angew. Chem. Int. Ed. 2005; 44: 376
- 2m Handbook of Functionalized Organometallics . Knochel P. Wiley-VCH; Weinheim: 2005
- 2n Hodgson DM, Miles SM. Angew. Chem. Int. Ed. 2006; 45: 935
- 3 Chen Q, Mollat du Jourdin X, Knochel P. J. Am. Chem. Soc. 2013; 135: 4958
- 4a Mosrin M, Knochel P. Chem. Eur. J. 2009; 15: 1468
- 4b Mosrin M, Knochel P. Org. Lett. 2008; 10: 2497
- 5 Monolikakes SM, Jaric M, Karaghiosoff K, Knochel P. Chem. Commun. 2013; 49: 2124
- 6a Wunderlich SH, Rohbogner CJ, Unsinn A, Knochel P. Org. Process Res. Dev. 2010; 14: 339
- 6b Rohbogner CJ, Wirth S, Knochel P. Org. Lett. 2010; 12: 1984
- 7 Mosrin M, Bresser T, Knochel P. Org. Lett. 2009; 11: 3406
- 8a Wunderlich S, Knochel P. Chem. Commun. 2008; 6387
- 8b Mosrin M, Knochel P. Org. Lett. 2009; 11: 1837
- 8c Crestey F, Knochel P. Synthesis 2010; 1097
- 9 Despotopoulou C, Klier L, Knochel P. Org. Lett. 2009; 11: 3326
- 10 Dunst C, Knochel P. J. Org. Chem. 2011; 76: 6972
- 11 Boudet N, Dubbaka SR, Knochel P. Org. Lett. 2008; 10: 1715
- 12 Hagg B, Mosrin M, Ila H, Malakhov V, Knochel P. Angew. Chem. Int. Ed. 2011; 50: 9794
- 14a Joule JA In Science of Synthesis . Vol. 10. Thomas EJ. Georg Thieme Verlag; Stuttgart: 2000. Chapt. 10.13, 361
- 14b Joule JA, Mills K. Heterocyclic Chemistry . John Wiley and Sons; New York: 2009. Chapt. 20, 373
- 14c Sundberg RJ. The Chemistry of Indoles . Academic Press; New York: 1970
- 14d Sundberg RJ. Indoles; 2nd ed.. Academic Press; London: 1996
- 14e Tyrrell E, Brookes P. Synthesis 2003; 469
- 15a Cacchi S, Fabrizi G. Chem. Rev. 2005; 105: 2873
- 15b Rewcastle GW, Katritzky AR. Adv. Heterocycl. Chem. 1993; 56: 155
- 15c Familoni OB. Synlett 2002; 1181
- 16a Somei M, Yamada F. Nat. Prod. Rep. 2004; 21: 278
- 16b Somei M, Yamada F. Nat. Prod. Rep. 2005; 22: 761
- 16c Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893 ; and references therein
- 16d Beller M, Breindl C, Riermeier TH, Tillack A. J. Org. Chem. 2001; 66: 1403 ; and references therein
- 17a Sundberg RJ. Comprehensive Heterocyclic Chemistry . Vol. 4. Katritzy AR, Rees CW. Peragamon; Oxford: 1984: 313
- 17b Sundberg RJ. Comprehensive Heterocyclic Chemistry II . Vol. 2. Katritzky AR, Rees CW, Scriven EF. V, Bird CW. Pergamon Press; Oxford: 1996: 119
- 17c Gribble GW. Comprehensive Heterocyclic Chemistry II . Vol. 2. Katritzky AR, Rees CW, Scriven EF. V, Bird CW. Pergamon Press; Oxford: 1996: 207
- 18 Baeyer A. Liebigs Ann. Chem. 1866; 140: 295
- 19a Gribble GW. J. Chem. Soc., Perkin Trans. 1 2000; 1045
- 19b Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 2001; 2491
- 19c Humphrey GR, Kuethe JT. Chem. Rev. 2006; 106: 2875
- 19d Gribble GW. Natural Product Synthesis . Vol. 1. Pearson WH. Jai Press; Greenwich CT: 1990: 43
- 20 Eisch JJ. Organometallics 2002; 21: 5439
- 21a Shirley DA, Roussel PA. J. Am. Chem. Soc. 1953; 75: 375
- 21b See also: Shevchenko NE, Nenajdenko VG, Balenkova ES. Synthesis 2003; 1191
- 22a Sundberg RJ, Russell HF. J. Org. Chem. 1973; 38: 3324
- 22b Wahlström N, Stensland B, Bergman J. Synthesis 2004; 1187
- 22c Kuethe JT, Wong A, Davies IW. Org. Lett. 2003; 5: 3721
- 22d Wu J.-P, Sanyal S, Lu Z.-H, Senanayake CH. Tetrahedron Lett. 2009; 50: 5667
- 22e Smart BP, Oslund RC, Walsh LA, Gelb MH. J. Med. Chem. 2006; 49: 2858
- 22f Mehboobi S, Uecker A, Cénac C, Sellmer A, Eichhorn E, Elz S, Böhmer F.-D, Dove S. Bioorg. Med. Chem. 2007; 15: 2187
- 22g Naka H, Akagi Y, Yamada K, Imahori T, Kasahara T, Kondo Y. Eur. J. Org. Chem. 2007; 4635
- 23 Hasan I, Marinelli ER, Lin L.-CC, Fowler FW, Levy AB. J. Org. Chem. 1981; 46: 157
- 24 Katritzky AR, Akutagawa K. Tetrahedron Lett. 1985; 26: 5935
- 25 Edwards MP, Doherty AM, Ley SV, Organ HM. Tetrahedron 1986; 42: 3723
- 26a Hlasta DJ, Bell MR. Heterocycles 1989; 29: 849
- 26b Katritzky AR, Lue P, Chen YX. J. Org. Chem. 1990; 55: 3688
- 27a Gmeiner P, Kraxner J, Bollinger B. Synthesis 1996; 1196
- 27b Kraxner J, Gmeiner P. Synthesis 2000; 1081
- 28 Gharpure M, Stoller A, Bellamy F, Firnau G, Snieckus V. Synthesis 1991; 1079
- 29 Takeda Y, Nishiyama H, Ishikura M, Kamata K, Terashima M. Heterocycles 1992; 33: 173
- 30a Merlic CA, Mclnnes DM, You Y. Tetrahedron Lett. 1997; 38: 6787
- 30b Ruhland T, Pedersen H, Andersen K. Synthesis 2003; 2236
- 30c Sakurada J, Satoh T. Tetrahedron 2007; 63: 3806
- 30d Kusurkar RS, Goswami SK. Tetrahedron 2004; 60: 5315
- 30e Ishikura M, Kato H, Ohnuki N. Chem. Commun. 2002; 220
- 30f Bernardo PH, Chai CL. L, Elix JA. Tetrahedron Lett. 2002; 43: 2939
- 30g Manabe S, Marui Y, Ito Y. Chem. Eur. J. 2003; 9: 1435
- 31a Kawasaki T, Kodama A, Nishida T, Shimizu K, Somei M. Heterocycles 1991; 32: 221
- 31b Somei M, Kobayashi T. Heterocycles 1992; 34: 1295
- 31c Sanz R, Ignacio JM, Castroviejo MP, Fańanás FJ. ARKIVOC 2007; (iv): 84
- 32 Cheng L, Liu L, Sui Y, Wang D, Chen Y.-J. Tetrahedron: Asymmetry 2007; 18: 1833
- 33 Shirani H, Bergman J, Janosik T. Tetrahedron 2009; 65: 8350
- 34 Shirani H, Janosik T. J. Org. Chem. 2007; 72: 8984
- 35 Jiang J, Gribble GW. Tetrahedron Lett. 2002; 43: 4115
- 36a Bisseret P, Thielges S, Bourg S, Miethke M, Marahiel MA, Eustache J. Tetrahedron Lett. 2007; 48: 6080
- 36b So CM, Yeung CC, Lau CP, Kwong FY. J. Org. Chem. 2008; 73: 7803
- 36c Ishikura M, Takahashi N, Yamada K, Abe T. Heterocycles 2008; 75: 107
- 36d Bennasar ML, Roca T, Garcia-Diaz D. J. Org. Chem. 2008; 73: 9033
- 37a Ishikura M, Matsuzaki Y, Agata I. Heterocycles 1997; 45: 2309
- 37b Vazquez E, Payack JF. Tetrahedron Lett. 2004; 45: 6549
- 37c de Koning CB, Michael JP, Rousseau A. J. Chem. Soc., Perkin Trans. 1 2000; 1705
- 37d Johnson CN, Stemp G, Anand N, Stephen SC, Gallagher T. Synlett 1998; 1025
- 37e Kudo N, Perseghini M, Fu GC. Angew. Chem. Int. Ed. 2006; 45: 1282
- 38 Vasquez E, Davies IW, Payack JF. J. Org. Chem. 2002; 67: 7551
- 39a Denmark SE, Baird JD, Regens CS. J. Org. Chem. 2008; 73: 1440
- 39b Denmark SE, Baird JD. Org. Lett. 2004; 6: 3649
- 39c Rataboul F, Zapf A, Jackstell R, Harkal S, Riermeier T, Monsees A, Dingerdissen U, Beller M. Chem. Eur. J. 2004; 10: 2983
- 39d Artemova NV, Chevykalova MN, Luzikov YN, Nifant’ev IE, Nifant’ev EE. Tetrahedron 2004; 60: 10365
- 40a Bergman J, Venemalm L. J. Org. Chem. 1992; 57: 2495
- 40b Katritzky AR, Le KN. B, Mohapatra PP. Synthesis 2007; 3141
- 40c Guianvarc’h D, Fourrey J.-L, Dau M.-ET. H, Guérineau V, Benhida R. J. Org. Chem. 2002; 67: 3724
- 40d Shirani H, Stensland B, Bergman J, Janosik T. Synlett 2006; 2459
- 41a Hudkins RL, Diebold JL, Marsh FD. J. Org. Chem. 1995; 60: 6218
- 41b Labadie SS, Teng E. J. Org. Chem. 1994; 59: 4250
- 41c Palmisano G, Santagostino M. Helv. Chim. Acta 1993; 76: 2356
- 41d Dandu R, Tao M, Josef KA, Bacon ER, Hudkins RL. J. Heterocycl. Chem. 2007; 44: 437
- 42 Fukuda T, Mine Y, Iwao M. Tetrahedron 2001; 57: 975
- 43 Kondo Y, Yoshida A, Sakamato T. J. Chem. Soc., Perkin Trans. 1 1996; 2331
- 44a Bresser T, Mosrin M, Monzon G, Knochel P. J. Org. Chem. 2010; 75: 4686
- 44b Rohbogner CJ, Wunderlich SH, Clososki GC, Knochel P. Eur. J. Org. Chem. 2009; 1781
- 44c L’Helgoual’ch J.-M, Seggio A, Chevallier F, Yonehara M, Jeanneau E, Uchiyama M, Mongin F. J. Org. Chem. 2008; 73: 177
- 45a Amat M, Llor N, Pshenichnyi G, Bosch J. ARKIVOC 2002; (v): 73
- 45b Amat M, Hadida S, Pshenichnyi G, Bosch J. J. Org. Chem. 1997; 62: 3158
- 45c Amat M, Hadida S, Bosch J. Tetrahedron Lett. 1993; 34: 5005
- 45d Liu S.-F, Wu Q, Schmider HL, Aziz H, Hu N.-X, Popović Z, Wang S. J. Am. Chem. Soc. 2000; 122: 3671
- 45e Herz H.-G, Queiroz MJ. R. P, Maas G. Synthesis 1999; 1013
- 46a Pena MA, Sestelo JP, Sarandeses LA. J. Org. Chem. 2007; 72: 1271
- 46b Bouissane L, Sestelo JP, Sarandeses LA. Org. Lett. 2009; 11: 1285
- 46c Naka H, Uchiyama M, Matsumoto Y, Wheatley AE. H, MacPartlin M, Morey JV, Kondo Y. J. Am. Chem. Soc. 2007; 129: 1921
- 46d Usui S, Hashimoto Y, Morey JV, Wheatley AE. H, Uchiyama M. J. Am. Chem. Soc. 2007; 129: 15102
- 47 Palmisano G, Santagostino M. Synlett 1993; 771
- 48a Whisler MC, MacNeil S, Snieckus V, Beak P. Angew. Chem. Int. Ed. 2004; 43: 2206
- 48b Mulvey RE, Mongin F, Uchiyama M, Kondo Y. Angew. Chem. Int. Ed. 2007; 46: 3802
- 48c Milburn RR, Snieckus V. Angew. Chem. Int. Ed. 2004; 43: 888
- 48d Anctil EJ.-G, Snieckus V. J. Organomet. Chem. 2002; 653: 150
- 48e Mulvey RE. Organometallics 2006; 25: 1060
- 48f Veith M, Wieczorek S, Fries K, Huch Z. Anorg. Allg. Chem. 2000; 626: 1237
- 49a Buttery CD, Jones RG, Knight DW. J. Chem. Soc., Perkin Trans. 1 1993; 1425
- 49b Buttery CD, Jones RG, Knight DW. Synlett 1991; 315
- 49c Fisher LE, Labadie SS, Reuter DC, Clark RD. J. Org. Chem. 1995; 60: 6224
- 50a Gribble GW, Fraser HL, Badenock JC. Chem. Commun. 2001; 805
- 50b Cai X, Snieckus V. Org. Lett. 2004; 6: 2293
- 50c Gribble GW, Keavy DJ, Davis DA, Saulnier MG, Pelcman B, Barden TC, Sibi MP, Olson ER, BelBruno JJ. J. Org. Chem. 1992; 57: 5878
- 50d Gribble GW, Jiang J, Liu Y. J. Org. Chem. 2002; 67: 1001
- 50e Gribble GW, Saulnier MG, Pelkey ET, Kishbaugh TL. S, Liu Y, Jiang J, Trujillo HA, Keavy DJ, Davis DA, Conway SC, Switzer FL, Roy S, Silva RA, Obaza-Nutaitis JA, Sibi MP, Moskalev NV, Barden TC, Chang L, Habeski WM, Pelcman B. Curr. Org. Chem. 2005; 9: 1493
- 51 James CA, Coelho AL, Gevaert M, Forgione P, Snieckus V. J. Org. Chem. 2009; 74: 4094
- 52a Abbiati G, Baccalli EM, Marchesini A, Rossi E. Synthesis 2001; 2477
- 52b Saulnier MG, Gribble GW. J. Org. Chem. 1982; 47: 2810
- 53a Sun L, Liebeskind LS. Tetrahedron Lett. 1997; 38: 3663
- 53b Sun L, Liebeskind LS. J. Am. Chem. Soc. 1996; 118: 12473
- 53c Sun L, Liebeskind LS. J. Org. Chem. 1995; 60: 8194
- 53d Fürstner A, Domostoj MM, Scheiper B. J. Am. Chem. Soc. 2006; 128: 8087
- 53e Gan T, Liu R, Yu P, Zhao S, Cook JM. J. Org. Chem. 1997; 62: 9298
- 54a Herbert JM, Maggiani M. Synth. Commun. 2001; 31: 947
- 54b Katritzky AR, Xie L. J. Org. Chem. 1995; 60: 3707
- 54c Merlic CA, McInnes DM. Tetrahedron Lett. 1997; 38: 7661
- 55a Kuethe JT, Comins DL. J. Org. Chem. 2004; 69: 2863
- 55b Andersson H, Das S, Gustafsson M, Olsson R, Almqvist F. Tetrahedron Lett. 2010; 51: 4218
- 55c Barbe G, Pelletier G, Charette AB. Org. Lett. 2009; 11: 3398
- 56 Kondo Y, Takazawa N, Yoshida A, Sakamoto T. J. Chem. Soc., Perkin Trans. 1 1995; 1207
- 57a Abarbri M, Thibonnet J, Bérillon L, Dehmel F, Rottländer M, Knochel P. J. Org. Chem. 2000; 65: 4618
- 57b Baron O, Knochel P. Angew. Chem. Int. Ed. 2005; 44: 3133
- 58a Yang X, Althammer A, Knochel P. Org. Lett. 2004; 6: 1665
- 58b Yang X, Knochel P. Synthesis 2006; 2618
- 59a Conway SC, Gribble GW. Heterocycles 1992; 34: 2095
- 59b Gribble GW, Allison BD, Conway SC, Saulnier MG. Org. Prep. Proced. Int. 1992; 24: 649
- 59c Gribble GW, Saulnier MG. J. Org. Chem. 1983; 48: 607
- 59d Gribble GW, Barden TC. J. Org. Chem. 1985; 50: 5900
- 60a Liu Y, Gribble GW. Tetrahedron Lett. 2000; 41: 8717
- 60b Liu Y, Gribble GW. J. Nat. Prod. 2002; 65: 748
- 61 Liu Y, Gribble GW. Tetrahedron Lett. 2001; 42: 2949
- 63 Klingebiel U, Luttke W, Noltemeyer M, Schmidt HG. J. Organomet. Chem. 1993; 456: 41
- 64a Gribble GW, Johnson DA. Tetrahedron Lett. 1987; 28: 5259
- 64b Lipińska T. Tetrahedron Lett. 2002; 43: 9565
- 65 Johnson DA, Gribble GW. Heterocycles 1986; 24: 2127
- 66a Yokoyama Y, Uchida M, Murakami Y. Heterocycles 1989; 29: 1661
- 66b Zhao Z, Jaworski A, Piel I, Snieckus V. Org. Lett. 2008; 10: 2617
- 69 Saulnier MG, Gribble GW. J. Org. Chem. 1982; 47: 757
- 70a Amat M, Hadida S, Sathyanarayana S, Bosch J. J. Org. Chem. 1994; 59: 10
- 70b Amat M, Hadida S, Sathyanarayana S, Bosch J. Org. Synth. 1997; 74: 248
- 70c Amat M, Sathyanarayana S, Hadida S, Bosch J. Heterocycles 1996; 43: 1713
- 70d Amat M, Hadida S, Bosch J. Tetrahedron Lett. 1994; 35: 793
- 71a Wynne JH, Stalick WM. J. Org. Chem. 2002; 67: 5850
- 71b Wynne JH, Stalick WM. J. Org. Chem. 2003; 68: 4845
- 71c Bernardo PH, Chai CL. L. J. Org. Chem. 2003; 68: 8906
- 71d Belley M, Scheigetz J, Dubé P, Dolman S. Synlett 2001; 222
- 72 Qi T, Qiu W, Liu Y, Zhang H, Gao X, Liu Y, Lu K, Du C, Yu G, Zhu D. J. Org. Chem. 2008; 73: 4638
- 73a Hoerrner RS, Askin D, Volante RP, Reider PJ. Tetrahedron Lett. 1998; 39: 3455
- 73b Nishida A, Miyashita N, Fuwa M, Nakagawa M. Heterocycles 2003; 59: 473
- 73c Li G, Wang E, Chen H, Li H, Liu Y, Wang PG. Tetrahedron 2008; 64: 9033
- 74 Claridge TD. W, Long JM, Brown JM, Hibbs D, Hursthouse MB. Tetrahedron 1997; 53: 4035 . For an earlier example of the 3-bromoindole bromine–lithium exchange, see ref. 59d
- 75 Jiang B, Yang C.-G. Heterocycles 2000; 53: 1489
- 76 Amat M, Seffar F, Llor N, Bosch J. Synthesis 2001; 267
- 77a Sugiyama H, Yokokawa F, Aoyama T, Shioiri T. Tetrahedron Lett. 2001; 42: 7277
- 77b Sala DG, Capozzo D, Izzo I, Giordano A, Iommazzo A, Spinella A. Tetrahedron Lett. 2002; 43: 8839
- 78a Pirrung MC, Li Z, Park K, Zhu J. J. Org. Chem. 2002; 67: 7919
- 78b Kasahara T, Kondo Y. Chem. Commun. 2006; 891
- 78c Choshi T, Yamada S, Sugino E, Kuwada T, Hibino S. J. Org. Chem. 1995; 60: 5899
- 79 Liu Y, Gribble GW. Tetrahedron Lett. 2002; 43: 7135
- 80 Ueda I, Nishiura M, Takahashi T, Eda K, Hashimoto M, Yamamura K. Tetrahedron Lett. 2006; 47: 8535
- 81a Staubitz A, Dohle W, Knochel P. Synthesis 2003; 233
- 81b Kneisel FF, Knochel P. Synlett 2002; 1799
- 81c Gommermann N, Koradin C, Knochel P. Synthesis 2002; 2143
- 81d Jensen AE, Dohle W, Sapountzis I, Lindsay DM, Vu VA, Knochel P. Synthesis 2002; 565
- 81e Krasovsky A, Knochel P. Angew. Chem. Int. Ed. 2004; 43: 3333
- 82a Sapountzis I, Knochel P. Angew. Chem. Int. Ed. 2004; 43: 897
- 82b Kondo Y, Yoshida A, Sato S, Sakamoto T. Heterocycles 1996; 42: 105
- 83a Sapountzis I, Lin W, Kofink CC, Despotopoulou C, Knochel P. Angew. Chem. Int. Ed. 2005; 44: 1654
- 83b Korn TJ, Knochel P. Synlett 2005; 1185
- 83c Mal SK, Bohé L, Achab S. Tetrahedron 2008; 64: 5904
- 83d Tricotet T, O’Shea DF. Chem. Eur. J. 2010; 16: 6678
- 84 Manolikakes G, Knochel P. Angew. Chem. Int. Ed. 2009; 48: 205
- 85a Sakamato T, Kondo Y, Takazawa N, Yamanaka H. Tetrahedron Lett. 1993; 34: 5955
- 85b Prasad AS. B, Stevenson TM, Citineni JR, Nyzam V, Knochel P. Tetrahedron 1997; 53: 7237
- 85c Gong L.-Z, Knochel P. Synlett 2005; 267
- 86a Metzger A, Piller FM, Knochel P. Chem. Commun. 2008; 5824
- 86b Piller FM, Appukkuttan P, Gavryushin A, Helm M, Knochel P. Angew. Chem. Int. Ed. 2008; 47: 6802
- 86c Piller FM. Metzger A, Schade MA, Haag BA, Gavryushin A, Knochel P. Chem. Eur. J. 2009; 15: 7192
- 86d Blümke T, Piller FM, Knochel P. Chem. Commun. 2010; 4082
- 87 Shade MA, Manolikakes G, Knochel P. Org. Lett. 2010; 12: 3648
- 88a Fukuda T, Maeda R, Iwao M. Tetrahedron 1999; 55: 9151
- 88b Iwao M, Kuraishi T. Heterocycles 1992; 34: 1031
- 88c Okada M, Sato I, Cho SJ, Suzuki Y, Ojika M, Dubnau D, Sakagami Y. Biosci. Biotechnol. Biochem. 2004; 68: 2374
- 89 Hartung CG, Fecher A, Chapell B, Snieckus V. Org. Lett. 2003; 5: 1899
- 90 Masters NF, Mathews N, Nechvatal G, Widdowson DA. Tetrahedron 1989; 45: 5955
- 91 Dickens MJ, Mowlem TJ, Widdowson DA, Slawin AM. Z, Williams DJ. J. Chem. Soc., Perkin Trans. 1 1992; 323
- 92a Fukuda T, Akashima H, Iwao M. Tetrahedron 2005; 61: 6886 ; and references therein
- 92b See also: Nagakawa K, Somei M. Heterocycles 1994; 39: 31
- 93 Iwao M. Heterocycles 1993; 36: 29
- 94a Shinohara H, Fukuda T, Iwao M. Tetrahedron 1999; 55: 10989
- 94b Iwao M, Ishibashi F. Tetrahedron 1997; 53: 51
- 95a Iwao M, Motoi O, Fukuda T, Ishibashi F. Tetrahedron 1998; 54: 8999
- 95b Moro-oka Y, Fukuda T, Iwao M. Tetrahedron Lett. 1999; 40: 1713
- 96a Meseguer B, Alonso-Díaz D, Griebenow N, Herget T, Waldmann H. Angew. Chem. Int. Ed. 1999; 38: 2902
- 96b Meseguer B, Alonso-Diaz D, Griebenow N, Herget T, Waldmann H. Chem. Eur. J. 2000; 6: 3943
- 97 Hayakawa Y, Singh M, Shibata N, Takeuchi Y, Kirk KL. J. Fluorine Chem. 1999; 97: 161
- 98 Iwao M, Motoi O. Tetrahedron Lett. 1995; 36: 5929
- 99 Pérez-Serrano L, Casarrubios L, Domínguez G, Freire G, Pérez-Castells J. Tetrahedron 2002; 58: 5407
- 100 Hurt CR, Lin R, Rapoport H. J. Org. Chem. 1999; 64: 225
- 101 Chauder B, Larkin A, Snieckus V. Org. Lett. 2002; 4: 815
- 102a Griffen EJ, Roe DG, Snieckus V. J. Org. Chem. 1995; 60: 1484
- 102b Kinsman AC, Snieckus V. Tetrahedron Lett. 1999; 40: 2453
- 102c Rousseau J.-F, Dodd RH. Heterocycles 2001; 55: 2289
- 102d Tois J, Koskinen A. Tetrahedron Lett. 2003; 44: 2093
- 103 Moro-oka Y, Iwakiri S, Fukuda T, Iwao M. Tetrahedron Lett. 2000; 41: 5225
- 104a Schlosser M, Ginanneschi A, Leroux F. Eur. J. Org. Chem. 2006; 2956
- 104b Schlosser M. Angew. Chem. Int. Ed. 2006; 45: 5432
- 105a Moyer MP, Shiurba JF, Rapoport H. J. Org. Chem. 1986; 51: 5106
- 105b Yang Y, Martin AR, Nelson DL, Regan J. Heterocycles 1992; 34: 1169
- 105c Takami H, Koshimura H, Kumazawa T. Heterocycles 1999; 51: 1119
- 106 Cherry K, Lebegue N, Leclerc V, Carato P, Yous S, Berthelot P. Tetrahedron Lett. 2007; 48: 5751
- 107a Feldman KS, Eastman KJ, Lessene G. Org. Lett. 2002; 4: 3525
- 107b Balle T, Andersen K, Vedsø P. Synthesis 2002; 1509
- 108a Li L, Martins A. Tetrahedron Lett. 2003; 44: 689
- 108b Li L, Martins A. Tetrahedron Lett. 2003; 44: 5987
- 109a Buszek KR, Luo D, Kondrashov M, Brown N, Vander Velde D. Org. Lett. 2007; 9: 4135
- 109b Brown N, Luo D, Vander Velde D, Yang S, Brassfield A, Buszek KR. Tetrahedron Lett. 2009; 50: 63
- 109c Brown N, Luo D, Decapo JA, Buszek KR. Tetrahedron Lett. 2009; 50: 7113
- 109d Buszek KR, Brown N, Luo D. Org. Lett. 2009; 11: 201
- 110 Andersson H, Banchelin TS.-L, Das S, Gustafsson M, Olsson R, Almqvist F. Org. Lett. 2010; 12: 284
- 111a Stadlbauer W In Science of Synthesis . Vol. 12. Neier R. Georg Thieme Verlag; Stuttgart: 2002. Chapt. 12.2, 227
- 111b Elguero J In Comprehensive Heterocyclic Chemistry II . Vol. 3. Katritzky AR, Rees CW, Scriven EF. S. Pergamon; Oxford: 1996: 1
- 111c Elguero J In Comprehensive Heterocyclic Chemistry . Vol. 5. Katritzky AR, Rees CW. Peragamon; Oxford: 1984: 167
- 112a Schmidt A, Beutler A, Snovydovych B. Eur. J. Org. Chem. 2008; 4073
- 112b Cerecetto H, Gerpe A, González M, Arán VJ, de Ocáriz CO. Mini-Rev. Med. Chem. 2005; 5: 869
- 113a Collot V, Varlet D, Rault S. Tetrahedron Lett. 2000; 41: 4363
- 113b Collot V, Bovy PR, Rault S. Tetrahedron Lett. 2000; 41: 9053
- 113c Arnautu A, Collot V, Ros JC, Alayrac C, Witulski B, Rault S. Tetrahedron Lett. 2002; 43: 2695
- 114a Welch WM, Hanau CE, Whalen WM. Synthesis 1992; 937
- 114b Frasca AR. Tetrahedron Lett. 1962; 3: 1115
- 114c Casey ML, Kemp DS, Paul KG, Cox DD. J. Org. Chem. 1973; 38: 2294
- 115 Yang X, Knochel P. Synlett 2004; 2303
- 116 Luo G, Chen L, Dubowchik G. J. Org. Chem. 2006; 71: 5392
- 117 Bunnell A, O’Yang C, Petrica A, Soth MJ. Synth. Commun. 2006; 36: 285
- 118 Danielson ME, Hays DS, Kshirsagar TA, Haraldson CA, Lundquist GD, Wurst JR, Lindstrom KJ, Mackey SS, Willie DJ, Heppner PD, Leir CM, Benson KE. J. Org. Chem. 2007; 72: 4570
- 119 Despotopoulou C, Gignoux C, McConnell D, Knochel P. Synthesis 2009; 3661
- 120a Grimmett MR In Science of Synthesis . Vol. 12. Neier R. Georg Thieme Verlag; Stuttgart: 2002. Chapt. 12.4; 52
- 120b Grimmett MR In Comprehensive Heterocyclic Chemistry II . Vol. 3. Katritzky AR, Rees CW, Scriven EF. S. Elsvier; Oxford: 1996: 77
- 120c Grimmett MR In Comprehensive Heterocyclic Chemistry . Vol. 5. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 345
- 120d Grimmett MR. Imidazoles and Benzimidazole Synthesis, In Best Synthetic Methods. Meth-Cohn O. Academic Press; London: 1997
- 121 Ooi HC, Suschitzky H. J. Chem. Soc., Perkin Trans. 1 1982; 2871
- 122 Katritzky AR, Akutagawa K. J. Org. Chem. 1989; 54: 2949
- 123 Carr AA, Hay DA, Kane JM, Staeger MA. J. Org. Chem. 1990; 55: 1399
- 124 Katritzky AR, Ramer WH, Lam JN. J. Chem. Soc., Perkin Trans. 1 1987; 775
- 125a Katritzky AR, Rewcastle GW, Fan W.-Q. J. Org. Chem. 1988; 53: 5685
- 125b Kuzmenko VV, Filatova TA, Pozharskic AF. Chem. Heterocycl. Comp. (Engl. Transl.) 1992; 28: 1009
- 126 Katritzky AR, Drewniak-Deyrup M, Lan X, Brunner F. J. Heterocycl. Chem. 1989; 26: 829
- 127 Hilf C, Bosold F, Harms K, Marsch M, Boche G. Chem. Ber./Recl. 1997; 130: 1213
- 128 Rivas FM, Giessert AJ, Diver ST. J. Org. Chem. 2002; 67: 1708
- 129 Wunderlich SH, Kienle M, Knochel P. Angew. Chem. Int. Ed. 2009; 48: 7256
- 130 Asakawa K.-i, Dannenberg JJ, Fitch KJ, Hall SS, Kadowaki C, Karady S, Kii S, Maeda K, Marcune BF, Mase T, Miller RA, Reamer RA, Tschaen DM. Tetrahedron Lett. 2005; 46: 5081
- 131 Park SB, Alper H. Org. Lett. 2003; 5: 3209
- 132 Walker SR, Carter EJ, Belinda CH, Morris JC. Chem. Rev. 2009; 109: 3080
- 133a Hetherington WM, Micheils RH, Eisenthal KL. Chem. Phys. Lett. 1979; 66: 230
- 133b Herbich J, Sepiol J, Waluk J. J. Mol. Struct. 1984; 114: 329
- 133c Wu Q, Esteghamatian M, Hu N, Popovic ZD, Enright G, Beeze SR, Wang S. Angew. Chem. Int. Ed. 1999; 38: 985 ; and references therein
- 134a Popowycz F, Mérour J.-Y, Joseph B. Tetrahedron 2007; 63: 8689
- 134b Le Hyaric M, Vieira de Almeida M, Nora de Souza MV. Quim. Nova 2002; 25: 1165
- 134c Song JJ, Reeves JT, Gallou F, Tan Z, Yee NK, Senanayake CH. Chem. Soc. Rev. 2007; 36: 1120
- 134d Review on 7-azaindole: Popowycz F, Routier S, Joseph B, Mérour J.-Y. Tetrahedron 2007; 63: 1031
- 135 Bisagni E, Chi Hung N, Lhoste JM. Tetrahedron 1983; 39: 1777
- 136 Dormoy J.-R, Heymes A. Tetrahedron 1993; 49: 2885
- 137 Praly-Deprez I, Rivalle C, Belehradek J, Huel C, Bisagni E. J. Chem. Soc., Perkin Trans. 1 1991; 3173
- 138 Lefoix M, Daillant J.-P, Routier S, Mérour J.-Y, Gillaizeau I, Couder G. Synthesis 2005; 3581
- 139 Kelly TA, McNeil DW, Rose JM, David E, Shih C.-K, Grob PM. J. Med. Chem. 1997; 40: 2430
- 140 Mahboobi S, Pongratz H, Hufsky H, Hockemeyer J, Frieser M, Lyssenko A, Paper DH, Bürgermeister J, Böhmer F.-D, Fiebig H.-H, Burger AM, Baasner S, Beckers T. J. Med. Chem. 2001; 44: 4535
- 141 Bracher F, Hildebrand D. Tetrahedron 1994; 50: 12329
- 142 Desarbre E, Coudret S, Meheust C, Mérour J.-Y. Tetrahedron 1997; 53: 3637
- 143a Álvarez M, Fernández D, Joule JA. Tetrahedron Lett. 2001; 42: 315
- 143b Ahaidar A, Fernández D, Danelón G, Cuevas C, Manzanares I, Albericio F, Joule JA, Álvarez M. J. Org. Chem. 2003; 68: 10020
- 144 Curtis NR, Kulagowski JJ, Leeson PD, Ridgill MP, Emms F, Freedman SB, Patel S, Patel S. Bioorg. Med. Chem. Lett. 1999; 9: 585
- 145 Mouaddib A, Joseph B, Hasnaoui A, Mérour J.-Y. Tetrahedron Lett. 1999; 40: 5853
- 146 Alvarez M, Fernández D, Joule JA. Synthesis 1999; 615
- 147a Kuo GH, Prouty C, DeAngelis A, Shen L, O’Neill DJ, Shah C, Connolly PJ, Murray WV, Conway BR, Cheung P, Westover L, Xu JZ, Look RA, Demarest KT, Emanuel S, Middleton SA, Jolliffe L, Beavers MP, Chen X. J. Med. Chem. 2003; 46: 4021
- 147b Kumar A, Say M, Boykin DW. Synthesis 2008; 707
- 148 Thibault C, L’Heureux A, Bhide RS, Ruel R. Org. Lett. 2003; 5: 5023
- 149 L’Heureux A, Thibault C, Ruel R. Tetrahedron Lett. 2004; 45: 2317
For the N-benzyl protecting group, see ref. 30c and:
For further applications of 2-lithiation of N-Boc-indole, see:
For other examples of Suzki coupling and reactions with indolyl-2-boronic acid, see:
For further examples of the use of N-lithiocarboxylate as protecting group, see ref. 22b and:
For other examples of reactions of 2-stannyl indole, see:
For further examples of direct 2-zincation of indole, see:
For examples of Negishi cross-coupling of 2-indolylzinc reagents, see:
For direct 2-cupration of indole, see:
For further examples of 3-amido as directing group for 2-lithiation of indole, see:
See also the review:
For an earlier example of 2-lithiation of 2-iodoindole, see:
See also:
For other examples of reactions of 2-lithioindole, see:
For related examples, see:
For a recent synthesis of semipervirine using the same strategey, see:
For further examples of 3-haloindole–lithium exchange, see ref. 40e and:
See also:
For an application of 3-indolyl Grignard reagent in the synthesis of grossularine-1, see:
For an earlier example of halogen–magnesium exchange with ethylmagnesium bromide, see:
For a 3-magnesium–zinc exchange in indole, see:
For a 3-magnesium–tin exchange:
See also:
For a recent example of the N-DEB directing group in 7-lithiation, see:
Reviews:
Recent reviews:
For biological activity of indazole derivatives, see:
See also:
For reviews on 4-,5-,6-azaindole, see: