Synthesis 2015; 47(13): 1905-1912
DOI: 10.1055/s-0034-1380516
paper
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted Synthesis of Fused and Substituted 2-Aminopyridines from β-Halo α,β-Unsaturated Aldehydes

Junali Gogoi
Medicinal Chemistry Division, CSIR-North East Institute of Science and Technology, Jorhat 785006, India   Email: gogoipranj@yahoo.co.uk   Email: rc_boruah@yahoo.co.in
,
Pranjal Gogoi*
Medicinal Chemistry Division, CSIR-North East Institute of Science and Technology, Jorhat 785006, India   Email: gogoipranj@yahoo.co.uk   Email: rc_boruah@yahoo.co.in
,
Limi Goswami
Medicinal Chemistry Division, CSIR-North East Institute of Science and Technology, Jorhat 785006, India   Email: gogoipranj@yahoo.co.uk   Email: rc_boruah@yahoo.co.in
,
Romesh C. Boruah*
Medicinal Chemistry Division, CSIR-North East Institute of Science and Technology, Jorhat 785006, India   Email: gogoipranj@yahoo.co.uk   Email: rc_boruah@yahoo.co.in
› Author Affiliations
Further Information

Publication History

Received: 27 November 2014

Accepted after revision: 09 March 2015

Publication Date:
21 April 2015 (online)


Abstract

2-Aminopyridines were synthesized from β-halo α,β-unsaturated aldehydes by a microwave-assisted Knoevenagel reaction. The β-halo-α,β-unsaturated aldehydes were, in turn, efficiently synthesized from the corresponding ketones by a Vilsmeier formylation reaction. The protocol was used to synthesize several novel steroidal and nonsteroidal fused 2-aminopyridine derivatives.

Supporting Information

 
  • References

    • 1a Jones G In Comprehensive Heterocyclic Chemistry II . Vol. 5. Katritzky AR, Rees CW, Scriven EF. V. Chap. 5.05 Pergamon; Oxford: 1996: 167
    • 1b Henry GD. Tetrahedron 2004; 60: 6043
    • 1c Michael JP. Nat. Prod. Rep. 2005; 22: 627
  • 2 Goetz AE, Garg NK. Nat. Chem. 2013; 5: 54
  • 3 Murata T, Shimada M, Sakakibara S, Yoshino T, Kadono H, Masuda T, Shimazaki M, Shintani T, Fuchikami K, Sakai K, Inbe H, Takeshita K, Niki T, Umeda M, Bacon KB, Ziegelbauer KB, Lowinger TB. Bioorg. Med. Chem. Lett. 2003; 13: 913
  • 4 Mantri M, de Graaf O, van Veldhoven J, Göblyös A, von Frijtag Drabbe Künzel JK, Mulder-Krieger T, Link R, de Vries H, Beukers MW, Brussee J, Ijzerman AP. J. Med. Chem. 2008; 51: 4449
  • 5 Deng J, Sanchez T, Mawsawi LQ. A, Dayam R, Yunes RA, Garofalo A, Bolger MB, Neamati N. Bioorg. Med. Chem. 2007; 15: 4985
  • 6 Hagmann WK, Caldwell CG, Chen P, Durette PL, Esser CK, Lanza TJ, Kopka IE, Guthikonda R, Shah SK, MacCoss M, Chabin RM, Fletcher D, Grant SK, Green BG, Humes JL, Kelly TM, Luell S, Meurer R, Moore V, Pacholok SG, Pavia T, Williams HR, Wong KK. Bioorg. Med. Chem. Lett. 2000; 10: 1975
  • 7 Huang H, Guzman-Perez A, Acquaviva L, Berry V, Bregman H, Dovey J, Gunaydin H, Huang X, Huang L, Saffran D, Serafino R, Schneider S, Wilson C, DiMauro EF. ACS Med. Chem. Lett. 2013; 4: 1218
    • 8a Perrier V, Wallace AC, Kaneko K, Safar J, Prusiner SB, Cohen FE. Proc. Natl. Acad. Sci. U.S.A. 2000; 97: 6073
    • 8b May BC. H, Zorn JA, Witkop J, Sherrill J, Wallace AC, Legname G, Prusiner SB, Cohen FE. J. Med. Chem. 2007; 50: 65
  • 9 Levy SB, Alekshun MN, Podlogar BL, Ohemeng K, Verma AK, Warchol T, Bhatia B, Bowser T, Grier M. US 2005124678, 2005
  • 10 Chen H, Zhang W, Tam R, Raney AK. WO 2005058315, 2005
  • 11 Younis Y, Douelle F, Feng T.-S, González Cabrera D, Le Manach C, Nchinda AT, Duffy S, White KL, Shackleford DM, Morizzi J, Mannila J, Katneni K, Bhamidipati R, Zabiulla KM, Joseph JT, Bashyam S, Waterson D, Witty MJ, Hardick D, Wittlin S, Avery V, Charman SA, Chibale K. J. Med. Chem. 2012; 55: 3479
    • 12a Cocco MT, Congiu C, Lilliu V, Onnis V. Eur. J. Med. Chem. 2005; 40: 1365
    • 12b Anderson DR, Stehle NW, Kolodziej SA, Reinhard EJ. WO 2004055015, 2004
  • 13 Koner RR, Sinha S, Kumar S, Nandi CK, Ghosh S. Tetrahedron Lett. 2012; 53: 2302
    • 14a Palani T, Park K, Kumar MR, Jung HM, Lee S. Eur. J. Org. Chem. 2012; 5038
    • 14b Zeng J, Tan YJ, Leow ML, Liu X.-W. Org. Lett. 2012; 14: 4386
    • 14c Ueda S, Nagasawa H. J. Am. Chem. Soc. 2009; 131: 15080
    • 14d Wang H, Wang Y, Peng C, Zhang J, Zhu Q. J. Am. Chem. Soc. 2010; 132: 13217
    • 14e Bentabed-Ababsa G, Ely SC. S, Hesse S, Nassar E, Chevallier F, Nguyen TT, Derdour A, Mongin F. J. Org. Chem. 2010; 75: 839
    • 14f Gulevich AV, Helan V, Wink DJ, Gevorgyan V. Org. Lett. 2013; 15: 956
    • 15a Katritzky AR, Rachwal S, Smith TP, Steel PJ. J. Heterocycl. Chem. 1995; 32: 979
    • 15b Thomas S, Roberts S, Pasumansky L, Gamsey S, Singaram B. Org. Lett. 2003; 5: 3867
    • 16a Chichibabin AE, Zeide OA. Zh. Russ. Fiz.-Khim. O-va., Chast Khim. 1914; 46: 1216
    • 16b Leffler MT. Org. React. (N. Y.) 1942; 1: 91
    • 16c Mcgill CK, Rappa A. Adv. Heterocycl. Chem. 1988; 44: 1
    • 17a Yin J, Xiang B, Huffman MA, Raab CE, Davies IW. J. Org. Chem. 2007; 72: 4554
    • 17b Londregan AT, Jennings S, Wei L. Org. Lett. 2010; 12: 5254
    • 18a Tu S, Jiang B, Jia YZ. R, Zhang J, Yao C, Shi F. Org. Biomol. Chem. 2007; 5: 355
    • 18b Salem MA. I, Madkour HM. F, Soliman El-SA, Mahmoud NF. H. Heterocycles 2000; 53: 1129
    • 18c Latif N, Girgis N. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1981; 20: 147
  • 19 Hu J, Zhang Q, Yuan H, Liu Q. J. Org. Chem. 2008; 73: 2442
    • 20a Wan Y, Yuan R, Zhang F.-R, Pang L.-L, Ma R, Yue C.-H, Lin W, Yin W, Bo R.-C, Wu H. Synth. Commun. 2011; 41: 2997
    • 20b Pagadala R, Maddila S, Moodley V, van Zyl WE, Jonnalagadda SB. Tetrahedron Lett. 2014; 55: 4006
  • 21 Sharma U, Ahmed S, Boruah RC. Tetrahedron Lett. 2000; 41: 3493
    • 22a Gogoi J, Bezbaruah P, Saikia P, Goswami J, Gogoi P, Boruah RC. Tetrahedron Lett. 2012; 53: 1497
    • 22b Bezbaruah P, Gogoi J, Rao KS, Gogoi P, Boruah RC. Tetrahedron Lett. 2012; 53: 4389
    • 22c Bezbaruah P, Gogoi P, Gogoi J, Boruah RC. Synthesis 2013; 45: 1341
    • 22d Gogoi J, Gogoi P, Bezbaruah P, Boruah RC. Tetrahedron Lett. 2013; 54: 7136
    • 22e Gogoi P, Bezbaruah P, Boruah RC. Eur. J. Org. Chem. 2013; 5032
    • 22f Gogoi J, Gogoi P, Boruah RC. Eur. J. Org. Chem. 2014; 3483