Synthesis 2014; 46(14): 1847-1852
DOI: 10.1055/s-0034-1378350
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

A Convenient Practical Synthesis of Alkyl and Aryl Oxime Esters

S. Chandrappa Santosh Kumar
Plantation Products, Spices and Flavour Technology Department, CSIR-Central Food Technological Research Institute, Mysore 570020, India   Fax: +91(821)2517233   Email: bettadaiah@cftri.res.in
,
Nanjundaswamy Vijendra Kumar
Plantation Products, Spices and Flavour Technology Department, CSIR-Central Food Technological Research Institute, Mysore 570020, India   Fax: +91(821)2517233   Email: bettadaiah@cftri.res.in
,
Pullabhatla Srinivas
Plantation Products, Spices and Flavour Technology Department, CSIR-Central Food Technological Research Institute, Mysore 570020, India   Fax: +91(821)2517233   Email: bettadaiah@cftri.res.in
,
Bheemanakere Kempaiah Bettadaiah*
Plantation Products, Spices and Flavour Technology Department, CSIR-Central Food Technological Research Institute, Mysore 570020, India   Fax: +91(821)2517233   Email: bettadaiah@cftri.res.in
› Author Affiliations
Further Information

Publication History

Received: 03 February 2014

Accepted after revision: 30 May 2014

Publication Date:
24 June 2014 (online)


Abstract

A facile access to the synthesis of alkyl and aryl oxime esters of ketoximes and aldoximes in high yields (90–97%) is reported. The reactions were performed using N-[3-(methylamino)propyl]-N′-ethylcarbodiimide hydrochloride (EDCI) reagent in the presence of 4-(dimethylamino)pyridine (DMAP) as a catalyst at room temperature. The isolation and purification of products is very simple and in cases where product is solid, column chromatography is avoided.

Supporting Information

 
  • References

    • 1a Zhukovskaya NA, Dikusar EA, Potkin VI, Vyglazov OG. Chem. Nat. Compd. 2009; 45: 148
    • 1b Zhukovskaya NA, Dikusar EA, Vyglazov OG. Chem. Nat. Compd. 2008; 44: 688
    • 1c Dikusar EA, Zhukovskya NA. Russ. J. Org. Chem. 2008; 44: 1389
  • 2 Lukasczyk A, Martin H, Diel PJ, Föry W, Gätzi K, Kristinsson H, Müller B, Muntwyler JP, Pachlatko H, Rempfler H, Schurter R, Szczepanski H. EP 0,012,158, 1980
  • 3 Crichlow GV, Cheng KF, Dabideen D, Ochani M, Aljabari B, Pavlov VA, Miller EJ, Lolis E, Al-Abed Y. J. Biol. Chem. 2007; 282: 3089
  • 4 Hayashi I, Shimizu K. Bull. Chem. Soc. Jpn. 1983; 56: 3197
  • 5 Bachovchin DA, Wolfe MR, Masuda K, Brown SJ, Spicer TP, Fernandez-Vega V, Chase P, Hodder PS, Rosen H, Cravatt BF. Bioorg. Med. Chem. Lett. 2010; 20: 2254
    • 6a Hwu JR, Tsay S, Hong SC, Hsu M, Liu C, Chou SP. Bioconjugate Chem. 2013; 24: 1778
    • 6b Bindu PJ, Mahadevan KM, Satyanarayan ND, Ravikumar Naik TR. Bioorg. Med. Chem. Lett. 2012; 22: 898
  • 7 Liu XH, Zhi LP, Song BA, Xu HL. Chem. Res. Chin. Univ. 2008; 24: 454
  • 8 Li TG, Liu JP, Han JT, Fu B, Wang DQ, Wang MG. Chin. J. Org. Chem. 2009; 29: 898
  • 9 Ma JA, Huang RQ, Chai YX. Prog. Nat. Sci. 2002; 12: 271
  • 10 Song BA, Liu XH, Yang S, Hu DY, Jin LH, Zhang YT. Chin. J. Org. Chem. 2005; 25: 507
  • 11 Gao Y, Song J, Shang S, Wang D, Li J. BioResources 2012; 7: 4150
  • 12 Wylie BB, Isaacson EI, Delgado GN. J. Pharm. Sci. 1965; 54: 1373
  • 13 Harini ST, Vijay Kumar H, Rangaswamy J, Naik N. Bioorg. Med. Chem. Lett. 2012; 22: 7588
  • 14 Karakurt A, Alagöz MA, Sayoğlu B, Çaliş Ü, Dalkara S. Eur. J. Med. Chem. 2012; 57: 275
  • 15 Kundu SK, Rahman M, Dhara P, Hajra A, Majee A. Synth. Commun. 2012; 42: 1848
  • 16 Enders D, Grossmann A, Craen DV. Org. Biomol. Chem. 2013; 11: 138
  • 17 Okada T, Kawanisi M, Nazaki H. Bull. Chem. Soc. Jpn. 1969; 42: 2981