2, 2, 2‐Trifluoroethyl Oxalates in the One‐Pot Parallel Synthesis of Hindered Aliphatic Oxamides1. Issue 12 (30th March 2016)

• Record Type: Journal Article
• Authors: Bogolubsky, Andrey V.; Moroz, Yurii S.; Mykhailiuk, Pavel K.; Pipko, Sergey E.; Grishchenko, Alexander V.; Zhemera, Anton V.; Konovets, Anzhelika I.; Doroschuk, Roman A.; Dmytriv, Yurii V.; Zaporozhets, Olga A.; Tolmachev, Andrey
• Is Part Of: European journal of organic chemistry. Issue 12(2016)
• Page Start: 2120
• Page End: 2130
• Publication Date: 2016-03-30
• Subjects: Synthetic methods -- Combinatorial chemistry -- Amides -- Amines -- Esters -- Aminolysis -- Steric hindrance; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501579
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A simple parallel synthesis approach to unsymmetrical N 1, N 2 ‐substituted aliphatic oxamides using methyl (2, 2, 2‐trifluoroethyl) oxalate and bis(2, 2, 2‐trifluoroethyl) oxalate was developed. The method was validated on a 52‐membered set of the oxamides, derived mainly from hindered primary and secondary aliphatic amines, and gave the products with a high overall success rate in moderate yields. Abstract : An approach to the synthesis of alkyl oxamides from hindered amines using trifluoroethyl oxalates was developed. Validation of the method on a millimolar scale gave the oxamides in multi‐milligram quantities.