Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2013; 45(5): 678-682
DOI: 10.1055/s-0032-1318149
DOI: 10.1055/s-0032-1318149
paper
Click Chemistry with 2-Ethynyl-4,5,6,7-tetrahydroindoles: Towards Functionalized Tetrahydroindole-Triazole Ensembles
Further Information
Publication History
Received: 02 December 2012
Accepted after revision: 11 January 2013
Publication Date:
01 February 2013 (online)
Abstract
2-Ethynyl-4,5,6,7-tetrahydroindoles, readily available from 4,5,6,7-tetrahydroindoles and bromoacetylenes on K2CO3, when treated with sodium azide in DMSO, afford functionalized tetrahydroindole-triazoles ensembles. The reaction proceeds under mild conditions (room temperature) to give triazoles with acyl or ester moieties in quantitative yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Kharb R, Sharma PCh, Yar MSh. J. Enzyme Inhib. Med. Chem. 2011; 26: 1
- 1b Singhal N, Sharma PK, Dudhe R, Kumar N. J. Chem. Pharm. Res. 2011; 3: 126
- 2a Bektaş H, Karaali N, Sahin D, Demirbaş A, Karaoglu SA, Demirbaş N. Molecules 2010; 15: 2427
- 2b Sumangala V, Poojary B, Chidananda N, Fernandes J, Kumari NS. Arch. Pharmacal. Res. 2010; 33: 1911
- 2c Pereira D, Fernandes P. Bioorg. Med. Chem. Lett. 2011; 21: 510
- 3a Savini L, Massarelli P, Chiasserini L, Pellerano C, Bruni G. Farmaco 1994; 49: 633
- 3b Almasirad A, Tabatabai SA, Faizi M, Kebriaeezadeh A, Mehrabi N, Dalvandi A, Shafiee A. Bioorg. Med. Chem. Lett. 2004; 14: 6057
- 3c Ram JS. Rasayan J. Chem. 2009; 2: 706
- 3d Rajasekaran A, Rajagopal KA. Acta Pharm. 2009; 59: 355
- 4a Singh BK, Yadav AK, Kumar B, Gaikwad A, Sinha SK, Chaturvedi V, Tripathi RP. Carbohydr. Res. 2008; 343: 1153
- 4b Wilkinson BL, Long H, Sim E, Fairbanks AJ. Bioorg. Med. Chem. Lett. 2008; 18: 6265
- 4c Boechat N, Ferreira VF, Ferreira SB, de Lourdes G, Ferreira M, de C da Silva F, Bastos MM, Dos S, Costa M, Lourenço MC, Pinto AC, Krettli AU, Aguiar AC, Teixeira BM, da Silva NV, Martins PR, Bezerra FA, Camilo AL, da Silva GP, Costa CC. J. Med. Chem. 2011; 54: 5988
- 5a Zhou L, Amer A, Korn M, Burda R, Balzarini J, De Clercq E, Kern ER, Torrence PF. Antiviral Chem. Chemother. 2005; 16: 375
- 5b Jordão AK, Afonso PP, Ferreira VF, de Souza MC, Almeida MC, Beltrame CO, Paiva DP, Wardell SM, Wardell JL, Tiekink ER, Damaso CR, Cunha AC. Eur. J. Med. Chem. 2009; 44: 3777
- 5c Pérez-Castro I, Caamaño O, Fernández F, García MD, López C, de Clercq E. ARKIVOC 2010; (iii): 152
- 6a Holla BS, Poojary KN, Rao BS, Shivananda MK. Eur. J. Med. Chem. 2002; 37: 511
- 6b Holla BS, Veerendra B, Shivananda MK, Poojary B. Eur. J. Med. Chem. 2003; 38: 759
- 6c Reddy DM, Srinivas J, Chashoo G, Saxena AK, Kumar HM. S. Eur. J. Med. Chem. 2011; 46: 1983
- 6d Singh P, Raj R, Kumar V, Mahajan MP, Bedi PM, Kaur T, Saxena AK. Eur. J. Med. Chem. 2012; 47: 594
- 6e Li X, Lin Y, Yuan Y, Liu K, Qian X. Tetrahedron 2011; 67: 2299
- 6f Kumar D, Narayanam MK, Chang K.-H, Shah K. Chem. Biol. Drug Des. 2011; 77: 182
- 7 Kaur H, Kumar S, Lata S, Saxena KK, Kumar A. Eur. J. Med. Chem. DOI: 10.1016/j.ejmech.2010.07.047.
- 8a Aher NG, Pore VS, Mishra NN, Kumar A, Shukla PK, Sharma A, Bhat MK. Bioorg. Med. Chem. Lett. 2009; 19: 759
- 8b Wei J.-J, Jin L, Wan K, Zhou Ch.-He. Bull. Korean Chem. Soc. 2011; 32: 229
- 8c Sangshetti JN, Lokwani DK, Sarkate AP, Shinde DB. Chem. Biol. Drug Des. 2011; 78: 800
- 8d Morzherin Y, Prokhorova PE, Musikhin DA, Glukhareva TV, Fan Z. Pure Appl. Chem. 2011; 83: 715
- 8e Shalini K, Kumar N, Drabu S, Sharma PK. Beilstein J. Org. Chem. 2011; 7: 668
- 8f Wang XL, Wan K, Zhou CH. Eur. J. Med. Chem. 2010; 45: 4631
- 9 Schreier E. Helv. Chim. Acta 1976; 59: 585
- 10 Dong H.-S, Wei K, Wang Q.-L, Quan B, Zhang Z.-Y. J. Chin. Chem. Soc. 2000; 47: 343
- 11a The Merck Index . 12th ed.; Budavari S. Merck Co. Inc; White House Station, NJ: 1996
- 11b Haber J. Cas. Lek. Cesk. 2001; 140: 596
- 12a Mothes-Wagner U, Reitze HK, Seitz KA. Exp. Appl. Acarol. 1990; 8: 27
- 12b Pechacek JT. US Patent 6015826 A, 1998 ; Chem. Abstr. 2000, 132, 89499.
- 12c Jacobson RM, Mulvihill MJ, Liu Ch, Liu X. US Patent 6258751, 2001 ; Chem. Abstr. 2001, 134, 42133.
- 13a Quraishi MA, Danish J. J. Am. Oil Chem. Soc. 2000; 77: 1107
- 13b Quraishi MA, Sardar R. Corrosion 2002; 58: 748
- 14a Khanmohammadi H, Erfantalab M. Spectrochim. Acta, Part A 2012; 86: 39
- 14b Smith NW, Alonso A, Brown CM, Dzyuba SV. Biochem. Biophys. Res. Commun. 2010; 391: 1455
- 15 Guenther D, Nestler HJ, Roesher G, Schinzel E. Ger. Pat. 615164, 1980 ; Chem. Abstr. 1980, 93, 73786.
- 16a Bijev AT, Prodanova P. Chem. Heterocycl. Compd. 2007; 43: 306
- 16b Padmavathi V, Nagendra MohanA. V, Thriveni P, Shazia A. Eur. J. Med. Chem. 2009; 44: 2313
- 17 Sessler JL, Cai J, Gong H.-Y, Yang X, Arambula JF, Hay BP. J. Am. Chem. Soc. 2010; 132: 14058
- 18a Kamijo S, Jin T, Huo Z, Yamamoto Y. J. Am. Chem. Soc. 2003; 125: 7786
- 18b Amantini D, Fringuelli F, Piermatti O, Pizzo F, Zunino E, Vaccaro L. J. Org. Chem. 2005; 70: 6526
- 18c Barluenga J, Valdés C, Beltrán G, Escribano M, Aznar F. Angew. Chem. Int. Ed. 2006; 45: 6893
- 18d Jiang Y, Kuang C, Yang Q. Synthesis 2010; 4256
- 18e Kolarovič A, Schnürch M, Mihovilovic MD. J. Org. Chem. 2011; 76: 2613
- 19a Journet M, Cai D, Kowal JJ, Larsen RD. Tetrahedron Lett. 2001; 42: 9117
- 19b Katritzky AR, Singh SK. J. Org. Chem. 2002; 67: 9077
-
19c Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 19d Katritzky AR, Zhang Y, Singh SK. Heterocycles 2003; 60: 1225
- 19e Li J, Wang D, Zhang Y, Li J, Chen B. Org. Lett. 2009; 11: 3024
- 19f Wu L.-Y, Xie Y.-X, Chen Z.-S, Niu Y.-N, Liang Y.-M. Synlett 2009; 1453
- 19g Zhang W, Kuang C, Yang Q. Synthesis 2010; 283
- 20a Trofimov BA, Stepanova ZV, Sobenina LN, Mikhaleva AI, Ushakov IA. Tetrahedron Lett. 2004; 45: 6513
- 20b Stepanova ZV, Sobenina LN, Mikhaleva AI, Ushakov IA, Elokhina VN, Voronov VK, Trofimov BA. Synthesis 2004; 2736
- 20c Sobenina LN, Demenev AP, Mikhaleva AI, Ushakov IA, Vasil'tsov AM, Ivanov AV, Trofimov BA. Tetrahedron Lett. 2006; 47: 7139
- 20d Trofimov BA, Sobenina LN, Stepanova ZV, Demenev AP, Mikhaleva AI, Ushakov IA, Vakul'skaya TI, Petrova OV. Russ. J. Org. Chem. 2006; 42: 1348
- 20e Trofimov BA, Sobenina LN, Stepanova ZV, Ushakov IA, Petrova OV, Tarasova OA, Volkova KA, Mikhaleva AI. Synthesis 2007; 447
- 20f Trofimov BA, Sobenina LN, Demenev AP, Stepanova ZV, Petrova OV, Ushakov IA, Mikhaleva AI. Tetrahedron Lett. 2007; 48: 4661
- 21a Trofimov BA, Sobenina LN, Stepanova ZV, Vakul'skaya TI, Kazheva ON, Aleksandrov GG, Dyachenko OA, Mikhaleva AI. Tetrahedron 2008; 64: 5541
- 21b Trofimov BA, Sobenina LN, Stepanova ZV, Petrova OV, Ushakov IA, Mikhaleva AI. Tetrahedron Lett. 2008; 49: 3946
- 22a Trofimov BA, Mikhaleva АI. N-Vinylpyrroles . Nauka; Novosibirsk: 1984
- 22b Trofimov BA In Advances in Heterocyclic Chemistry . Vol. 51. Academic Press; New York: 1990: 177
- 22c Trofimov BA, Mikhaleva АI, Schmidt EYu, Ryapolov OA, Platonov VB. Russian Patent RU 2297410, 2006 ; Chem. Abstr. 2008, 146, 462130.