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Synthesis of 5-aryl-$N$-(trichloroacetyl)-1,3,4-oxadiazole-2-carboxamide via three-component reaction of trichloroacetyl isocyanate, ($N$-isocyanimino)triphenylphosphorane, and benzoic acid derivatives
Author(s) -
Nahid Shajari,
Ali Reza Kazemizadeh,
Ali Ramazani
Publication year - 2015
Publication title -
turkish journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.239
H-Index - 46
eISSN - 1303-6130
pISSN - 1300-0527
DOI - 10.3906/kim-1501-43
Subject(s) - chemistry , benzoic acid , aryl , isocyanate , carboxamide , medicinal chemistry , carbon 13 nmr , oxadiazole , organic chemistry , alkyl , polyurethane
The three-component reaction of benzoic acid derivatives, ($N$-isocyanimino)triphenylphosphorane, and trichloroacetyl isocyanate in a 1:1:1 ratio in CH$_{3}$CN occurred at room temperature, and the 5-aryl-$N$-(trichloroacetyl)-1,3,4-oxadiazole-2-carboxamide derivatives produced were formed in high yields. The reaction proceeded smoothly and cleanly under mild reaction conditions and no side reactions were observed. The structures of the products were confirmed by IR, $^{1}$H NMR, $^{13}$C NMR, mass spectroscopy, and elemental analysis.

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