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

Junali Gogoi; Pranjal Gogoi; Limi Goswami; Romesh C. Boruah

doi:10.1055/s-0034-1380516

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(13): 1905-1912
DOI: 10.1055/s-0034-1380516

paper

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

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Abstract

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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.

Key words

steroids - pyridines - enals - Knoevenagel reactions - cyclizations

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Referenzen

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

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