Synthesis 2015; 47(23): 3701-3710
DOI: 10.1055/s-0035-1560208
paper
© Georg Thieme Verlag Stuttgart · New York

New and Efficient Synthesis of 2,3,4-Trisubstituted 2H-Pyrrolo[3,4-c]quinolines via a MCR/Staudinger/Aza-Wittig Sequence

Feng Qu
a   College of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang, 441053, Hubei Province, P. R. of China
,
Ruo-Fei Hu
a   College of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang, 441053, Hubei Province, P. R. of China
,
Le Gao
a   College of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang, 441053, Hubei Province, P. R. of China
,
Jing Wu
a   College of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang, 441053, Hubei Province, P. R. of China
,
Xiao-Hong Cheng
b   Hubei Key Laboratory of Low Dimensional Optoelectronic Materials and Devices, Hubei University of Arts and Science, Xiangyang, 441053, Hubei Province, P. R. of China
,
Song Wang
b   Hubei Key Laboratory of Low Dimensional Optoelectronic Materials and Devices, Hubei University of Arts and Science, Xiangyang, 441053, Hubei Province, P. R. of China
,
Ping He*
a   College of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang, 441053, Hubei Province, P. R. of China
b   Hubei Key Laboratory of Low Dimensional Optoelectronic Materials and Devices, Hubei University of Arts and Science, Xiangyang, 441053, Hubei Province, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 07 July 2015

Accepted after revision: 14 August 2015

Publication Date:
01 September 2015 (online)


Abstract

A new and efficient method for the construction of 2,3,4-trisubstituted 2H-pyrrolo[3,4-c]quinoline derivatives was developed. Starting from easily accessible 2-azidobenzaldehyde, nitromethane, 1,3-dicarbonyl compounds, and various amines gave the multicomponent reaction (MCR) products, 1-substituted 3-acyl-4-(2-azidophenyl)-2-methyl-1H-pyrroles, that underwent Staudinger/aza-Wittig cyclization of in the presence of triphenylphosphine to give the final products.

Supporting Information

 
  • References

    • 1a Domling A. Chem. Rev. 2006; 106: 17
    • 1b Domling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083
    • 1c Wessjohann LA, Rivera DG, Vercillo OE. Chem. Rev. 2009; 109: 796
    • 1d Touré BB, Hall DG. Chem. Rev. 2009; 109: 4439
    • 1e Brauch S, van Berkel SS, Westermann B. Chem. Soc. Rev. 2013; 42: 4948
  • 2 Akbarzadeh R, Amanpour T, Bazgir A. Tetrahedron 2014; 70: 8142
  • 3 Welsch SJ, Umkehrer M, Kalinski C, Ross G, Burdack C, Kolb J, Wild M, Ehrlich A, Wessjohann L. Tetrahedron Lett. 2015; 56: 1025
  • 4 Ramazani A, Rezaei A. Org. Lett. 2010; 12: 2852
  • 5 Corres N, Delgado JJ, García VM, Marcaccini S, Rodríguez T, Josefa Rojo J, Torroba T. Tetrahedron 2008; 64: 2225
  • 6 He P, Nie YB, Wu J, Ding MW. Org. Biomol. Chem. 2011; 9: 1429
    • 7a Sańudo M, García VM, Marcaccini S, Delgado JJ, Rojo J, Torroba T. J. Org. Chem. 2009; 74: 2189
    • 7b Pertejo P, Corres N, Torroba T, María GV. Org. Lett. 2015; 17: 612
    • 7c Wang Y, Chen M, Ding MW. Tetrahedron 2013; 69: 9056
  • 8 Furlotti G, Alisi MA, Apicella C, Capezzone JA, Cazzolla N, Costi R, Cuzzucoli CG, Garrone B, Iacovo A, Magarò G, Mangano G, Miele G, Ombrato R, Pescatori L, Polenzani L, Rosi F, Vitiello M, Di Santo R. J. Med. Chem. 2012; 55: 9446
  • 9 Campaigne E, Hutchinson JH. J. Heterocycl. Chem. 1970; 7: 655
  • 10 Ganjian I, Khorshidi M, Lalezari I. J. Heterocycl. Chem. 1991; 28: 1173
    • 11a Kravchenko DV, Kydil VM, Tkachenko SE, Maliarchouk S, Okum IM, Ivachtchenko AV. Farmaco 2005; 60: 804
    • 11b Kravchenko DV, Kydil VM, Tkachenko SE, Maliarchouk S, Okum IM, Ivachtchenko AV. Eur. J. Med. Chem. 2005; 40: 1377
    • 11c Kravchenko DV, Kysil VV, Ilyn AP, Tkachenko SE, Maliarchouk S, Okum IM, Ivachtchenko AV. Bioorg. Med. Chem. Lett. 2005; 15: 1841
  • 12 Kravchenko DV, Kuzovkova YA, Kysil VM, Tkachenko SE, Maliarchouk S, Okum IM, Balakin KV, Ivachtchenko AV. J. Med. Chem. 2005; 48: 3680

    • Reports for the synthesis of pyrrolo[3,4-c]quinolines
    • 13a Pintér Á, Nyerges M, Virányi A, Tőke L. Tetrahedron Lett. 2003; 44: 2343
    • 13b Nyerges M, Pintér Á, Virányi A, Blaskó G, Tőke L. Tetrahedron 2005; 61: 8199
    • 13c Afarinkia K, Ansari Mo R, Bird CW, Gyambibi I. Tetrahedron Lett. 1996; 37: 4801
    • 13d Fritz H, Schenk S. Liebigs Ann. Chem. 1975; 255
    • 13e Kim SC, Gowrisankar S, Kim JN. Tetrahedron Lett. 2006; 47: 3463
    • 13f Roy RB, Swan GA. J. Chem. Soc. C 1969; 1886
    • 13g Khandelwal GD, Swan GA, Roy RB. J. Chem. Soc., Perkin Trans. 1 1974; 891
    • 13h Ivachtchenko AV, Kobak VV, Il’yin AP, Trifilenkov AS, Busel AA. J. Comb. Chem. 2003; 5: 645
    • 13i Veenstra SJ, Fortgens HP, Vijn RJ, de Jong BS, Speckamp WN. Tetrahedron 1987; 43: 1147
    • 13j Virányi A, Nyerges M, Blaskó G, Tőke L. Synthesis 2003; 2655
    • 14a Lee ES, Park JG, Jahng Y. Tetrahedron Lett. 2003; 44: 1883
    • 14b Osborne D, Stevenson PJ. Tetrahedron Lett. 2002; 43: 5469
  • 15 Liu GS, Dong QL, Yao YS, Yao ZJ. Org. Lett. 2008; 10: 5393
    • 16a Bharate JB, Sharma R, Aravinda S, Gupta VK, Singh B, Bharate SB, Vishwakarma RA. RSC Adv. 2013; 3: 21736
    • 16b Li BL, Li PH, Fang XN, Li CX, Sun JL, Mo LP, Zhang ZH. Tetrahedron 2013; 69: 7011
    • 16c Reddy GR, Reddy TR, Joseph SC, Reddy KS, Pal M. RSC Adv. 2012; 2: 3387
    • 16d Li BL, Zhang M, Hu HC, Du X, Zhang ZH. New J. Chem. 2014; 38: 2435
    • 16e Maiti S, Biswas S, Jana U. J. Org. Chem. 2010; 75: 1674
    • 16f Khan AT, Lal M, Bagdi PR, Basha RS, Saravanan P, Patra S. Tetrahedron Lett. 2012; 53: 4145
    • 16g Hu HC, Liu YH, Li BL, Cui ZS, Zhang ZH. RSC Adv. 2015; 5: 7720
    • 17a Sarkar S, Bera K, Jalal S, Jana U. Eur. J. Org. Chem. 2013; 27: 6055
    • 17b Zhang F, Li C, Qi C. Synthesis 2013; 45: 3007
    • 17c Silveira CC, Mendes SR, Martins GM, Schlösser SC, Kaufman TS. Tetrahedron 2013; 69: 9076
    • 17d Arai M, Miyauchi Y, Miyahara T, Ishikawa T, Saito S. Synlett 2009; 122
    • 18a Saeidian H, Abdoli M, Salimi R. C. R. Chim. 2013; 16: 1063
    • 18b Jalal S, Sarkar S, Bera K, Maiti S, Jana U. Eur. J. Org. Chem. 2013; 4823
    • 19a He P, Wu J, Nie YB, Ding MW. Tetrahedron 2009; 65: 8563
    • 19b He P, Wu J, Nie YB, Ding MW. Eur. J. Org. Chem. 2010; 1088
    • 19c Li WJ, Liu S, He P, Ding MW. Tetrahedron 2010; 66: 8151
    • 19d Wu J, Liu JC, Wang L, Ding MW. Synlett 2011; 2880
    • 20a Zhou BH, Yang J, Li MH, Gu YL. Green Chem. 2011; 13: 2204
    • 20b Yang J, Li HQ, Li MH, Peng JJ, Gu YL. Adv. Synth. Catal. 2012; 354: 688
    • 20c Yang J, Zhou BH, Li MH, Gu YL. Tetrahedron 2013; 69: 1057
  • 21 Bräse S, Gil C, Knepper K, Zimmermann V. Angew. Chem. Int. Ed. 2005; 44: 5188