ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7

Published monthly
 

Addition-cyclization reactions of (Z)-2,3-diphenylpropenoyl isothiocyanate with aniline and diphenylamine

M. Dzurilla, P. Kutschy, P. Kristian, and D. Koščik

Department of Organic Chemistry, Faculty of Natural Sciences, P. J. Šafárik University, CS-041 67 Košice

 

Abstract: The reaction of (Z)-2,3-diphenylpropenoyl isothiocyanate with aniline and diphenylamine has been studied. The stable thiourea, formed in the reaction with aniline, in the presence of Lewis acid (BF3 • Et20) cyclizes to cis 5,6-diphenyl-2-phenylamino-5,6-dihydro-4H-1,3-thiazin-4-one. In alkali medium cis-l,3-thiazine undergoes Dimroth rearrangement under forma­tion of cis-l,5,6-triphenyl-2-thiouracil. N-Phenyl-N'-(2,3-diphenylpropenoyl)thiourea at similar conditions affords a mixture of cis- and trans-2-thiouracils. In the reaction with triethylamine both isomers can be iso­lated. Isomerization of trans-2-thiouracil tc the cis isomer has been studied simultaneously. Diphenylamine with 2,3-diphenylpropenoyl isothiocyanate gives a mixture of cis- and trans-l,3-thiazines. It was impossible to isolate the corresponding thiourea as cis-l,3-thiazine was formed already at low temperature.

Full paper in Portable Document Format: 442a221.pdf

 

Chemical Papers 44 (2) 221–228 (1990)

Saturday, October 23, 2021

IMPACT FACTOR 2020
2.097
SCImago Journal Rank 2020
0.344
SEARCH
Advanced
VOLUMES
XXVIII. International Conference on Coordination and Bioinorganic Chemistry
© 2021 Chemical Papers