Convenient preparation of A-ring fused pyridines from steroidal enamides

Steroids

Volumn 73, Issue 11, 2008, Pages 1137-1142

  Barthakur, Madan G ^a   Borthakur, Moyurima ^a   Boruah, Romesh C ^a  

^a CSIR NORTH EAST INSTITUTE OF SCIENCE AND TECHNOLOGY   (India)

Author keywords

Chloromethyleneiminium salt; Formylation; Pyridosteroid; Steroidal enamide; Vilsmeier reaction

Indexed keywords

6' CHLORO 5ALPHA CHOLEST[3,2 B]PYRIDINE; AMIDE; CARBENOID; CHLOROMETHYLENEIMINIUM SALT; PYRIDINE DERIVATIVE; PYRIDOSTEROID DERIVATIVE; REAGENT; STEROID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FORMYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; VILSMEIER REACTION; X RAY ANALYSIS;

ANAEROBIOSIS; CHEMISTRY, ORGANIC; CRYSTALLOGRAPHY, X-RAY; HEAT; MOLECULAR CONFORMATION; PYRIDINES; STEROIDS;

EID: 46749115458     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2008.04.016     Document Type: Article

References (23)

1. Singh H., Jindal D.P., Yadav M.R., and Kumar M. Heterosteroids and drug research. Prog Med Chem 28 (1991) 233-300
2. Akhrem A.A., Lakhvich F.A., Lis L.G., and Kuz'mitskii B.B. Complete synthesis, structure, and function of 8-azasteroids-a new class of biologically active compounds. Vestsi Akademii Navuk BSSR. Seryya Khimichnykh Navuk 6 (1982) 81-90
3. Hirshmann R., Steinberg N.G., Buchschacher P., Fried J.H., Kent G.J., Tishler M., et al. Synthesis and structure of steroidal 4-pregneno[3,2-c]pyrazoles. A novel class of potent anti-inflammatory steroids. J Am Chem Soc 85 (1963) 120-122
4. Burbiel J., and Bracher F. Azasteroids as antifungals. Steroids 68 (2003) 587-594
5. Clinton R.O., Manson A.J., Stonner F.W., Beyler A.L., Potts G.O., and Arnold A. Steroidal[3,2-c]pyrazoles. J Am Chem Soc 81 (1959) 1513-1514
6. Clinton R.O., Manson A.J., Stonner F.W., Beyler A.L., Potts G.O., and Arnold A. Communications. Steroidal[2,3-d]isoxazoles. J Org Chem 26 (1961) 279
7. Chelucci G., Gladiali S., and Marchetti M. A three-step pyridoannelation of carbonyl compounds. J Heterocycl Chem 25 (1988) 1761-1765
8. Ackermann J.H., Potts G.O., Beyler A.L., and Clinton R.O. Steroidal heterocycles. X1. Steroidal[3,2-d]pyrimidines and related compounds. J Med Chem 7 (1964) 238-240
9. Laitonjam W.S., Rajkumar T.S., and Chingakham B.S. Synthesis of some A- and D-ring fused steroidal pyrazoles, isoxazoles and pyrimidines. Steroids 67 (2002) 203-209
10. Zhang X.-Q., and Sui Z.-H. An efficient synthesis of novel estrieno[2,3-b] and [3,4-c]pyrroles. Tetrahedron Lett 44 (2003) 3071-3073
11. Manson A.J., Stonner F.W., Neumann H.C., Christensen R.G., Clarke R.L., Ackermann J.H., et al. Steroidal heterocycles. VII. Androstano[2,3-d]isoxazoles and related compounds. J Med Chem 6 (1963) 1-9
12. Gupta R., Pathak D., and Jindal D.P. Synthesis and biological activity of azasteroidal[3,2-c]- and [17,16-c]pyrazoles. Eur J Med Chem 31 (1996) 241-247
13. Yan J.-H., Li J., and Rao G.-W. One-pot synthesis of new A-ring fused steroidal pyridines. Steroids 72 (2007) 736-739
14. Boger D.L., and Nakahara S. Diels-Alder reaction of N-sulfonyl-1-aza-1,3-butadienes: development of a synthetic approach to streptonigrin. J Org Chem 56 (1991) 880-884
15. Lin S., and Danishefsky S.J. The total synthesis of proteasome inhibitors TMC-95A and TMC-95B: discovery of a new method to generate cis-propenyl amides. Angew Chem Int Ed 41 (2002) 512-515
16. Musso D.L., Cochran F.R., Kelley J.L., McLean E.W., Selph J.L., Rigdon G.C., et al. Indanylidenes. 1. Design and synthesis of (E)-2-(4,6-difluro-1-indanylidene) acetamide, a potent centrally acting muscle relaxant with inflammatory and analgesic activity. J Med Chem 46 (2003) 399-408
17. Feldgus S., and Landis C.R. Origin of enantioreversal in the rhodium-catalyzed asymmetric hydrogenation of prochiral enamides and the effect of the α-substituent. Organometallics 20 (2001) 2374-2386
18. Boar R.B., McGhie J.F., Robinson M., Barton D.H.R., Horwell D.C., and Stick R.V. A simple synthesis of enamides from ketoximes. J Chem Soc Perkin 1 (1975) 1237-1241
19. Morzycki J.W., Lotowski Z., Stepniowska M., Gryszkiewicz A., and Wilczewska A.Z. Nitration of N-acetyl enamines with acetyl nitrate. Tetrahedron 47 (1997) 16161-16168
20. Borthakur M., Barthakur M.G., and Boruah R.C. Microwave promoted one-pot synthesis of novel A-ring fused steroidal dehydropiperazines. Steroids 73 (2008) 539-542
21. Saikia A., Barthakur M.G., Borthakur M., Saikia C.J., Bora U., and Boruah R.C. Conjugate base catalysed one-pot synthesis of pyrazoles from β-formyl enamides. Tetrahedron Lett 47 (2006) 43-46
22. Cheng Y.-S., Liu W.-L., and Chen S.-H. Pyridinium chlorochromate adsorbed on alumina as a selective oxidant for primary and secondary alcohols. Synthesis (1980) 223-224
23. Meth-Cohn O., and Taylor D.L. A novel one-step synthesis of quinolinium salts and 4-quinolones from formanilides. Tetrahedron Lett 34 (1993) 3629-3632