Sodium cyanoborohydride-mediated direct conversion of some heterocyclic aldehydes to esters

Synthetic Communications

Volumn 41, Issue 17, 2011, Pages 2505-2510

  Goswami, Shyamaprosad ^a   Hazra, Anita ^a   Goh, Jia Hao ^b   Fun, Hoong Kun ^b  

^a INDIAN INSTITUTE OF ENGINEERING SCIENCE AND TECHNOLOGY   (India)

^b SCHOOL OF PHYSICS   (Malaysia)

Author keywords

Esterification; Heterocyclic aldehydes; Heterocyclic esters; Sodium cyanoborohydride

Indexed keywords

ALDEHYDE DERIVATIVE; AMMONIUM CHLORIDE; CHLOROFORM; CYANOBOROHYDRIDE SODIUM; ESTER DERIVATIVE; HETEROCYCLIC COMPOUND; METHANOL; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; CRYSTAL STRUCTURE; DISTILLATION; OXIDATION; SPECTROSCOPY;

EID: 79959988360     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.502988     Document Type: Article

References (21)

1. Borch, R. F.; Durst, H. D. Lithium cyanohydridoborate, a versatile new reagent. J. Am. Chem. Soc. 1969, 91, 3996-3997
2. Weiss, M. J.; Grudzinskas, C. V. Prostaglandins and congeners, IV: The synthesis of certain 11-substituted derivatives of 11-deoxyprostaglandin E2 and F2α from 15-O-acetylprostaglandin A2 methyl ester. Tetrahedron Lett. 1973, 14, 141-144
3. Lane, C. F. Sodium cyanoborohydride: A highly selective reducing agent for organic functional groups. Synthesis 1975, 135-146.
4. Gidley, M. J.; Sanders, K. M. Reductive methylation of proteins with sodium cyanoborohydride: Identification, suppression, and possible uses of N-cyanomethyl byproducts. Biochem. J. 1982, 203, 331-334
5. Hutchins, R. O.; Kandasamy, D. Reductions of conjugated carbonyl compounds with cyanoborohydride in acidic media. J. Org. Chem. 1975, 40, 2530-2533.
6. Manescalchi, F.; Nardi, A. R.; Savoia, D. Reductive amination of 1,4- and 1,5-dicarbonyl compounds with (S)-valine methyl ester: Synthesis of (S)-2-phenylpyrrolidine and (S)-2-phenylpiperidine. Tetrahedron Lett. 1994, 35, 2775-2778 (Pubitemid 24137948)
7. Brown, H. C. Organic Syntheses via Boranes; Wiley-Interscience: New York, 1975
8. Taylor, E. J.; Djerassi, C. Mechanism of the sodium cyanoborohydride reduction of a,b-unsaturated tosylhydrazones. J. Am. Chem. Soc. 1976, 98, 2275-2281.
9. Borch, R. F.; Bernstein, M. D.; Durst, H. D. Cyanohydridoborate anion as a selective reducing agent. J. Am. Chem. Soc. 1971, 93, 2897-2904
10. Baxter, E. W.; Reitz, A. B. Reductive aminations of carbonyl compounds with borohydride and borane reducing agents. In Organic Reactions; Wiley: New York, 2002; vol. 59
11. Hutchins, R. O.; Milewski, C. A.; Maryanoff, B. E. Selective deoxygenation of ketones and aldehydes including hindered systems with sodium cyanoborohydride. J. Am. Chem. Soc. 1973, 95, 3662-3668.
12. Pelletier, S. W.; Mody, N. V.; Venkov, A. P.; Desai, H. K. Sodium cyanoborohydride: A reagent for selective reduction of the oxazolidine ring of C20-diterpenoid alkaloids. Tetrahedron Lett. 1979, 20, 4939-4940
13. Elliger, C. A. Deoxygenation of aldehydes and ketones with sodium cyanoborohydride. Synth. Commun. 1985, 15, 1315-1324.
14. Mattson, R. J.; Pham, K. M.; Leuck, D. J.; Cowen, K. A. An improved method for reductive alkylation of amines using titanium(IV) isopropoxide and sodium cyanoborohydride. J. Org. Chem. 1990, 55, 2552-2554.
15. Listvan, V. N.; Listvan, V. V.; Shekel, A. N. Synthesis of cholesteryl esters of heterocyclic analogs of cinnamic acid and hetaroyloxycinnamic acids by the Wittig reaction. Chem. Heterocycl. Comp. 2002, 38, 1480-1483
16. Li, D. Z.; Li, Y.; Chen, X. G.; Zhu, C. G.; Yang, J.; Liu, H. Y.; Pan, X. D. Synthesis and antitumor activity of heterocyclic acid ester derivatives of 20S-camptothecins. Chin. Chem. Lett. 2007, 18, 1335-1338.
17. Goswami, S.; Hazra, A. One-step direct conversion of heterocyclic aldehydes to esters. Chem. Lett. 2009, 38, 484
18. Mitsukura, K.; Sato, Y.; Yoshida, T.; Nagasawa, T. Oxidation of heterocyclic and aromatic aldehydes to the corresponding carboxylic acids by Acetobacter and Serratia strains. Biotechnol. Lett. 2004, 26, 1643-1648. (Pubitemid 40145591)
19. Bruker. APEX2, SAINT, and SADABS. Bruker AXS Inc.: Madison, WI, 2009
20. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr., Sect. A 2008, 64, 112-122
21. Spek, A. L. Structure validation in chemical crystallography. Acta Crystallogr., Sect. D 2009, 65, 148-155.