TY - JOUR

T1 - Synthesis and reactions of aromatic and heterocyclic isocyanides

AU - Mironov, M. A.

AU - Mokrushin, V. S.

PY - 1999

Y1 - 1999

N2 - Reactions of halo-and nitroanilines with dichlorocarbene resulted in formation of the corresponding isocyanides in poor yields. Better results are obtained by treatment with phosphoryl chloride of formanilides having the same substituents. The latter procedure was used to prepare previously inaccessible derivatives of 2-pyridyl, 2-thiazolyl, and 1,3,4-thiadiazol-2-yl isocyanides. To prevent polymerization, the isocyanides were isolated as complexes with copper(I) bromide which can be decomposed with aqueous potassium cyanide to release free isocyanides. Aryl and heteryl isocyanides reacted with such nucleophiles as water and dimethylamine under mild conditions.

AB - Reactions of halo-and nitroanilines with dichlorocarbene resulted in formation of the corresponding isocyanides in poor yields. Better results are obtained by treatment with phosphoryl chloride of formanilides having the same substituents. The latter procedure was used to prepare previously inaccessible derivatives of 2-pyridyl, 2-thiazolyl, and 1,3,4-thiadiazol-2-yl isocyanides. To prevent polymerization, the isocyanides were isolated as complexes with copper(I) bromide which can be decomposed with aqueous potassium cyanide to release free isocyanides. Aryl and heteryl isocyanides reacted with such nucleophiles as water and dimethylamine under mild conditions.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=0033241186

M3 - Article

VL - 35

SP - 693

EP - 697

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 5

ER -