A Convenient Practical Synthesis of Alkyl and Aryl Oxime Esters

S. Chandrappa Santosh Kumar; Nanjundaswamy Vijendra Kumar; Pullabhatla Srinivas; Bheemanakere Kempaiah Bettadaiah

doi:10.1055/s-0034-1378350

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(14): 1847-1852
DOI: 10.1055/s-0034-1378350

practical synthetic procedures

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

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

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.

Key words

oxime esters - aldoximes - ketoximes - EDCI - esterification - dehydration

Volltext

Referenzen

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

Zusatzmaterial

Supporting Information