Synthesis and regioselective [4+2] cycloaddition/nucleophilic reactions of N-arylamino-1:3-diaza-1:3-butadienes with ketenes and accompanying rearrangements

Autor:	Paramita D. Dey, Arun Sharma, Mohinder P. Mahajan, Sachchida N. Rai
Rok vydání:	1995
Předmět:	Nucleophile Chemistry Organic Chemistry Drug Discovery Regioselectivity Biochemistry Medicinal chemistry Cycloaddition
Zdroj:	Tetrahedron. 51:7459-7468
ISSN:	0040-4020
DOI:	10.1016/0040-4020(95)00372-f
Popis:	N-Arylamino-1:3-diaza-1:3-butadienes 4 are shown to undergo regioselective reactions with phenyl- and chloroketenes resulting in high yields of 3-aryl-2-methylthio6-phenyl-4(3H)-pyrimidinones 7 . Similar reactions with bromo- and iodoketenes, resulted, via aziridinium intermediates 12 , in good yields of 3-aryl-S-(N-arylamino)-2-methylthio-6-phenyl4(3H)-pyrimidinones 13 , The mechanistic aspects of cycloadditions and semi-empirical AM1 calculations for these diazabutadienes are also reported.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::d42d01009fbf1f4fa490adfaa1b804ca https://doi.org/10.1016/0040-4020(95)00372-f Zobrazit plný text záznamu Full Text from ScienceDirect