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Synthesis 2017; 49(07): 1603-1612
DOI: 10.1055/s-0036-1588366
DOI: 10.1055/s-0036-1588366
paper
Synthesis of Pyrido-Fused Imidazo[4,5-c]quinolines by I2-DMSO Promoted Oxidative Cross Coupling and Intramolecular Cyclization
Further Information
Publication History
Received: 20 September 2016
Accepted after revision: 08 November 2016
Publication Date:
07 December 2016 (online)
Abstract
The synthesis of a series of novel quinoline fused imidazo[4,5-c]quinolines was accomplished by a simple, efficient, iodine–dimethyl sulfoxide (I2–DMSO) promoted sequential oxidative cross coupling followed by intramolecular cyclization of pyridoimidazole arylamines and carbonyl compounds in a one-pot reaction. Simple reaction conditions, no metal catalyst, no additives, no ligand, selective product formation and high yields are the advantages of this method.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588366.
- Supporting Information
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References
- 1a Palmer AM, Grobbel B, Jecke C, Brehm C, Zimmermann PJ, Buhr W, Feth MP, Simon WA, Kromer W. J. Med. Chem. 2007; 50: 6240
- 1b Miller CM, McCarthy FO. RSC Adv. 2012; 2: 8883
- 1c Izuhra D, Swager TM. J. Am. Chem. Soc. 2009; 131: 17724
- 1d Zajac M, Hrobárik P, Magdolen P, Foltínová P, Zahradník P. Tetrahedron 2008; 64: 10605
- 2a Brase S, Gil C, Knepper K. Bioorg. Med. Chem. Lett. 2002; 10: 2415
- 2b Balaban AT, Oniciu DC, Katritzky AR. Chem. Rev. 2004; 104: 2777
- 3a Anderson EA. Org. Biomol. Chem. 2011; 9: 3997
- 3b Shao Z, Peng FZ. Curr. Org. Chem. 2011; 15: 4144
- 4a Kianmehr E, Ghanbari M, Niri MN, Faramarzi R. J. Comb. Chem. 2010; 12: 41
- 4b Jain AN. J. Med. Chem. 2004; 47: 947
- 4c Harrison TS, Keating GM. CNS Drugs 2005; 19: 65
- 4d Hanson SM, Morlock EV, Satyshur KA, Czajkowski C. J. Med. Chem. 2008; 51: 7243
- 4e Almirante L, Polo L, Mugnaini A, Provinciali E, Rugarli P, Biancotti A, Gamba A, Murmann W. J. Med. Chem. 1965; 8: 305
- 4f Linton A, Kang P, Ornelas M, Kephart S, Hu Q, Pairish M, Jiang Y, Guo C. J. Med. Chem. 2011; 54: 7705
- 5 Upadhayaya RS, Vandavasi JK, Kardile RA, Lahore SV, Dixit SS, Deokar HS, Shinde PD, Sarmah MP, Chattopadhyaya J. Eur. J. Med. Chem. 2010; 45: 1854
- 6 Eswaran S, Adhikari AV, Kumar RA. Eur. J. Med. Chem. 2010; 45: 957
- 7 Eswaran S, Adhikari AV, Pal NK, Chowdhury IH. Bioorg. Med. Chem. Lett. 2010; 20: 1040
- 8 Eswaran S, Adhikari AV, Shetty NS. Eur. J. Med. Chem. 2009; 44: 4637
- 9 Yang CL, Tseng CH, Chen YL, Lu CM, Kao CL, Tseng HY, Wu MH, Tzeng CC. Eur. J. Med. Chem. 2010; 45: 602
- 10 Tseng CH, Tzeng CC, Yang CL, Lu PJ, Chen HL, Li HY, Chuang YC, Yang CN, Chen YL. J. Med. Chem. 2010; 53: 6164
- 11 Chen YW, Chen YL, Tseng CH, Liang CC, Yang CN, Yao YC, Lu PJ, Tzeng CC. J. Med. Chem. 2011; 54: 4446
- 12 Tseng CH, Chen YL, Yang CL, Cheng CM, Han CH, Tzeng CC. Bioorg. Med. Chem. 2012; 20: 4397
- 13 Chang FS, Chen WC, Wang CH, Tzeng CC, Chen YL. Bioorg. Med. Chem. 2010; 18: 124
- 14 Tseng CH, Chen YL, Chung KY, Wang CH, Peng SI, Cheng CM, Tzeng CC. Org. Biomol. Chem. 2011; 9: 3205
- 15 Tseng CH, Chen YL, Hsu CY, Chen TC, Cheng CM, Tso HC, Lu YJ, Tzeng CC. Eur. J. Med. Chem. 2013; 59: 274
- 16 Koh EJ, EI-Gamal MI, Oh CH, Lee SH, Sim T, Kim G, Choi HS, Hong JH, Lee S, Yoo KH. Eur. J. Med. Chem. 2013; 70: 10
- 17 Arafa RK, Hegazy GH, Piazza GA, Abadi AH. Eur. J. Med. Chem. 2013; 63: 826
- 18 Ahmed N, Brahmbhatt KG, Sabde S, Mitra D, Singh IP, Bhutani KK. Bioorg. Med. Chem. 2010; 18: 2872
- 19 Peng HK, Lin CK, Yang SY, Tseng CK, Tzeng CC, Lee JC, Yang SC. Bioorg. Med. Chem. Lett. 2012; 22: 1107
- 20 Parkinson T, Pryde DC. Fut. Med. Chem. 2010; 2: 1181
- 21 Tseng CH, Lin CK, Chen YL, Hsu CY, Wu HN, Tseng CK, Lee JC. Eur. J. Org. Chem. 2014; 66
- 22 Adhikary PK, Das SK. J. Med. Chem. 1976; 19: 1352
- 23 Pandey AK, Sharma R, Shivahare R, Arora A, Rastogi N, Gupta S, Chauhan PM. S. J. Org. Chem. 2013; 78: 1534
- 24 Sharma S, Saha B, Sawant D, Kundu B. J. Comb. Chem. 2007; 9: 783
- 25a Anand Kumar P, Sharma R, Singh A, Shukla S, Srivastava K, Puri SK, Kumar B, Chauhan PM. S. RSC Adv. 2014; 4: 26757
- 25b Kielesiński Ł, Tasior M, Gryko DT. Org. Chem. Front. 2015; 2: 21
- 25c Avik Kumar B, Sougata S, Kamarul M, Alakananda H. Chem. Commun. 2015; 51: 1555
- 25d Kasiviswanadharaju P, Pinku K, Khima P, Anil K. Synthesis 2015; 47: 887
- 26 Fan X.-S, Zhang J, Bin L, Zhang X.-Y. Chem. Asian J. 2015; 10: 1281
- 27a Narender Reddy E, Chiranjeevi B, Sudha Sravanti K, Ramesh U, Jagadeesh Babu N, Krishnaiah A. Bioorg. Med. Chem. Lett. 2015; 25: 2918
- 27b Ashok K, Madhu Ch, Chiranjeevi B, Jagadeesh Babu N, Krishnaiah A. Org. Biomol. Chem. 2016; 14: 582
- 28 Madhu Ch, Narender Reddy E, Chiranjeevi B, Krishnaiah A. RSC Adv. 2015; 5: 19418