Versatile synthesis of 4-spiro-β-lactam-3-carbonitriles via the intramolecular nucleophilic cyclization of N-(p-hydroxyphenyl)cyanoacetamides
A series of 4-spiro-cyclohexadienonyl-β-lactam-3-carbonitriles, 2,7-dioxo-1-azaspiro[3.5]nona-5,8-diene-3-carbonitriles, was synthesized in satisfactory to excellent yields via the intramolecular nucleophilic cyclization of N-(p-hydroxyphenyl)cyanoacetamides with iodobenzene diacetate (IBD) as oxidant and potassium hydroxide as base. Acetic 4-spiro-cyclohexadienonyl- β-lactam-3-carbimidic anhydrides were obtained when organic base triethylamine was applied instead of potassium hydroxide. The mechanisms of the intramolecular nucleophilic cyclization and formation of acetic β-lactam-3-carbimidic anhydrides were proposed. The cyclization is a sequence of nucleophilic ipso addition and oxidative dearomatization. The formation of acetic carbimidic anhydrides is an acid-catalyzed acetate addition to the nitriles.
Abdellaoui, Hassane,Xu, Jiaxi
p. 4323 - 4330
(2014/06/10)
SYNTHESIS AND STUDY OF THE LIGHT-STABILIZING ACTIVITY OF SOME DITHIOCARBAMATES THAT INCLUDE A HETEROAROMATIC RING
A number of new dithiocarbamates of transition metals that contain thiophene, furan, benzothiophene, and benzoselenophene rings were synthesized.The compounds obtained were investigated as light stabilizers for polymers.It is shown that the effectiv
Gol'dfarb, Ya. L.,Ostapenko, E'. G.,Ivanov, V.B.,Efremkin, A. F.,Litvinov, V. P.
p. 1148 - 1153
(2007/10/02)
More Articles about upstream products of 123558-04-3