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C ‐Phosphorylated N ‐(Trichloroethylidene)sulfonamides: A New Type of Highly Electrophilic Imines
Author(s) -
Rassukana Yuliya V.,
Onys’ko Petro P.,
Davydova Kateryna O.,
Sinitsa Anatolii D.
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400086
Subject(s) - chemistry , electrophile , intramolecular force , adduct , nucleophile , medicinal chemistry , phosphorylation , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry
A convenient preparative approach to previously unknown, highly electrophilic C ‐phosphorylated N ‐arylsulfonylimines 1 , based on fairly readily accessible α‐phosphorylated sulfonamides 5 , has been developed. Compounds 1 react with trialkyl phosphites or ethyl diphenylphosphinite in the aza‐Perkow reaction scheme to give C , N ‐diphosphorylated N ‐dichlorovinylsulfonamides 8 . On treatment with O‐ and S‐nucleophilic agents (alcohols, thiols, thiophenols), 1 forms addition products 12 and 15 , the functionalized derivatives of α‐aminophosphonic acids, while interaction between 1 and mercaptoacetic acid proceeds with intramolecular cyclization of the intermediate adduct to produce the novel 2‐phosphorylated thiazolidinones 17 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)