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(1): 111-117
DOI: 10.1055/s-0032-1317781
DOI: 10.1055/s-0032-1317781
paper
A One-Pot Transition-Metal-Free Tandem Process to 1,4-Benzodiazepine Scaffolds
Further Information
Publication History
Received: 31 August 2012
Accepted after revision: 16 November 2012
Publication Date:
30 November 2012 (online)
Abstract
An efficient and practical method for the synthesis of 1,4-benzodiazepines is reported. This methodology offers a transition-metal-free tandem process in one pot. This process is applicable to the construction of a wide variety of 1,4-benzodiazepines and other tricyclic systems with high potential biological and pharmacological activities.
Key words
1,4-benzodiazepines - pyridazinobenzodiazepines - one-pot reaction - transition-metal-free tandem processSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 These authors contributed equally to this work.
- 2a Monro AM, Quinton RM, Wrigley TI. J. Med. Chem. 1963; 6: 255
- 2b Huang A, Liu F, Zhan C, Liu Y, Ma C. Org. Biomol. Chem. 2011; 9: 7351
- 2c Liu Y, Chu C, Huang A, Zhan C, Ma Y, Ma C. ACS Comb. Sci. 2011; 13: 547
- 3a Capuano B, Crosby IT, Lloyd EJ, Taylor DA. Aust. J. Chem. 2002; 55: 565
- 3b Liao Y, DeBoer P, Meier E, Wikström H. J. Med. Chem. 1997; 40: 4146
- 4 Coyne WE, Cusic JW. J. Med. Chem. 1967; 10: 541
- 5a Hasvold LA, Wang L, Przytulinska M, Xiao Z, Chen Z, Gu W.-Z, Merta PJ, Xue J, Kovar P, Zhang H, Park C, Sowin TJ, Rosenberg SH, Lin N.-H. Bioorg. Med. Chem. Lett. 2008; 18: 2311
- 5b Murugesan N, Gu Z, Lee V, Webb ML, Liu EC.-K, Hermsmeier M, Hunt JT. Bioorg. Med. Chem. Lett. 1995; 5: 253
- 6 Thuston DE, Bose DS. Chem. Rev. 1994; 94: 433
- 7a Breslin HJ, Kukla MJ, Ludovici DW, Mohrbacher R, Ho W, Miranda M, Rodgers JD, Hitchens TK, Leo G, Gauthier DA, Ho CY, Scott MK, De Clercq E, Pauwels R, Andries K, Janssen MA. C, Janssen PA. J. Med. Chem. 1995; 38: 771
- 7b Kukla MJ, Breslin HJ, Diamond CJ, Grous PP, Ho CY, Miranda M, Rodgers JD, Sherrill RG, De Clercq E, Pauwels R, Andries K, Moens LJ, Janssen MA. C, Janssen PA. J. J. Med. Chem. 1991; 34: 3187
- 8 Albright JD, Feich MF, Santos EG. D, Dusza JP, Sum FW, Venkatesan AM, Coupet J, Chan PS, Ru X, Mazandarani H, Bailey T. J. Med. Chem. 1998; 41: 2442
- 9a Capuano B, Crosby IT, McRobb FM, Podloucka A, Taylor DA, Vom A, Yuriev E. Aust. J. Chem. 2010; 63: 116
- 9b Matloubi H, Ghandi M, Zarrindast M.-R, Saemian N. Appl. Radiat. Isot. 2001; 55: 789
- 9c Sasikumar TK, Burnett DA, Zhang H, Smith-Torhan A, Fawzi A, Lachowicz JE. Bioorg. Med. Chem. Lett. 2006; 16: 4543
- 9d Hunziker F, Kunzle F, Schmutz J, Schindler O. Helv. Chim. Acta 1964; 47: 1163
- 9e Hunziker F, Fischer E, Schmutz J. Helv. Chim. Acta 1967; 50: 1588
- 9f Schmutz J, Kunzle F, Hunziker F, Gauch R. Helv. Chim. Acta 1967; 50: 245
- 9g Liao Y, Venhuis BJ, Rodenhuis N, Timmerman W, Wikström H. J. Med. Chem. 1999; 42: 2235
- 10a Sridhara AM, Reddy KR. V, Keshavayya J, Goud PS. K, Somashekar BC, Bose P, Peethambar SK, Gaddam SK. Eur. J. Med. Chem. 2010; 45: 4983
- 10b Prime ME, Courtney SM, Brookfield FA, Marston RW, Walker V, Warne J, Boyd AE, Kairies NA, Saal W, Limberg A, Georges G, Engh RA, Goller B, Rueger P, Rueth M. J. Med. Chem. 2011; 54: 312
- 10c Del OlmoE, Barboza B, Ybarra MI, Lopez-Perez JL, Carron R, Sevilla MA, Boselli C, San FelicianoA. Bioorg. Med. Chem. Lett. 2006; 16: 2786
- 10d Napoletano M, Norcini G, Pellacini F, Marchini F, Morazzoni G, Ferlenga P, Pradella L. Bioorg. Med. Chem. Lett. 2000; 10: 2235
- 10e Ma C, Liu SJ, Xin L, Falck JR, Shin DS. Tetrahedron 2006; 62: 9002
- 10f Cho SD, Song SY, Park YD, Kim JJ, Joo WH, Shiro M, Falck JR, Shin DS, Yoon YJ. Tetrahedron Lett. 2003; 44: 8995
- 10g Ma C, Cho SD, Falck JR, Shin DS. Synth. Commun. 2004; 34: 1399
- 10h Liu Y, Ma Y, Zhan C, Huang A, Ma C. Synlett 2012; 23: 255
- 10i Huang A, Qiao Z, Zhang X, Yu W, Zheng Q, Ma Y, Ma C. Tetrahedron 2012; 68: 906
- 11 Sayed GH, Sayed MA, Mahmoud MR, Shaaban SS. Egypt. J. Chem. 2002; 45: 767 ; Chem. Abstr. 2003, 141, 243501
- 12 Piaz VD, Ciciani G, Giovannoni MP. Synthesis 1994; 669
- 13 Katrusiak B, Unlu S, Banoglu E, Kupeli E, Yesilada E, Sahin MF. Arch. Pharm. (Weinheim, Ger.) 2003; 336: 406
- 14 Verhelst T, Verbeeck S, Ryabtsova O, Depraetere S, Maes BU. W. Org. Lett. 2011; 13: 272
- 15a Svete J. J. Heterocycl. Chem. 2005; 42: 361
- 15b Schwartz A, Beke G, Kovári Z, Böcskey Z, Farkas Ö, Mátyus P. J. Mol. Struct. 2000; 528: 49
- 16a Nardi M, Cozza A, De Nino A, Oliverio M, Procopio A. Synthesis 2012; 44: 800
- 16b Tiberghien AC, Evans DA, Kiakos K, Martin CR. H, Hartley JA, Thurston DE, Howard PW. Bioorg. Med. Chem. Lett. 2008; 18: 2073
- 16c Beccalli EM, Broggini G, Paladino G, Penoni A, Zoni C. J. Org. Chem. 2004; 69: 5627
- 16d Okubo T, Yoshikawa R, Chaki S, Okuyama S, Nakazato A. Bioorg. Med. Chem. 2004; 12: 3569
- 17 Wang L, Sullivan GM, Hexamer LA, Hasvold LA, Thalji R, Przytulinska M, Tao Z.-F, Li G, Chen Z, Xiao Z, Gu W.-Z, Xue J, Bui M.-H, Merta P, Kovar P, Bouska JJ, Zhang H, Park C, Stewart KD, Sham HL, Sowin TJ, Rosenberg SH, Lin N.-H. J. Med. Chem. 2007; 50: 4162
- 18 Joshua AV, Sharma SK, Strelkov A, Scott JR, Martin-Iverson MT, Abrams DN, Silverstone PH, McEwan AJ. B. Bioorg. Med. Chem. Lett. 2007; 17: 4066
- 19 Diao X, Xu L, Zhu W, Jiang Y, Wang H, Guo Y, Ma D. Org. Lett. 2011; 13: 6422
- 20a Su J, Tang H, McKittrick BA, Burnett DA, Zhang H, Smith-Torhan A, Fawzi A, Lachowicz J. Bioorg. Med. Chem. Lett. 2006; 16: 4548
- 20b Zhao H.-Y, Liu G. J. Comb. Chem. 2007; 9: 1164
- 20c Elmore CS, Dorff PN, Heys JR. J. Label. Compd. Radiopharm 2010; 53: 787
- 20d Al-Tel TH, Al-Qawasmeh RA, Schmidt MF, Al-Aboudi A, Rao SN, Sabri SS, Voelter W. J. Med. Chem. 2009; 52: 6484
- 20e Broggini G, Marchi ID, Martinelli M, Paladino G, Penoni A. Lett. Org. Chem. 2004; 1: 221
- 20f Hanze AR, Strube RE, Greig ME. J. Med. Chem. 1963; 6: 767
- 20g Beccalli EM, Broggini G, Paladino G, Zoni C. Tetrahedron 2005; 61: 61
- 20h Zhang L, Meier W, Wats E, Costello TD, Ma P, Ensinger CL, Rodgers JM, Jacobson IC, Rajagopalan P. Tetrahedron Lett. 1995; 36: 8387
- 21a Levy O, Erez M, Varon D, Keinan E. Bioorg. Med. Chem. Lett. 2001; 11: 2921
- 21b Basolo L, Beccalli EM, Borsini E, Broggini G, Khansaa M, Rigamonti M. Eur. J. Org. Chem. 2010; 9: 1694
- 21c Tsvelikhovsky D, Buchwald SL. J. Am. Chem. Soc. 2011; 133: 14228
- 21d Lu S.-M, Alper H. J. Am. Chem. Soc. 2005; 127: 14776
- 21e Bunce RA, Schammerhorn JE. J. Heterocycl. Chem. 2006; 43: 1031
- 21f Tardibono LP, Miller MJ. Org. Lett. 2009; 11: 1575
- 21g Majumdar KC, Ganai S. Synlett 2011; 1881
- 22a Leyva-Pérez A, Cabrero-Antonino JR, Corma A. Tetrahedron 2010; 66: 8203
- 22b Binaschi M, Boldetti A, Gianni M, Maggi CA, Gensini M, Bigioni M, Parlani M, Giolitti A, Fratelli M, Valli C, Terao M, Garattini E. ACS Med. Chem. Lett. 2010; 1: 411
- 23a Tu T, Wang Z, Liu Z, Feng X, Wang Q. Green Chem. 2012; 14: 921
- 23b Mahiwal K, Kumar P, Narasimhan B. Med. Chem. Res. 2012; 21: 293
- 24 Ma C, Liu S-J, Xin L, Falck JR, Shin D-S. Tetrahedron 2006; 62: 9002