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[3+3] Annulation via Ring Opening/Cyclization of Donor–Acceptor Cyclopropanes with (Un)symmetrical Ureas: A Quick Access to Highly Functionalized Tetrahydropyrimidinones
Author(s) -
Taily Irshad Maajid,
Saha Debarshi,
Banerjee Prabal
Publication year - 2019
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.201901400
Subject(s) - chemistry , annulation , electrophile , nucleophile , lewis acids and bases , combinatorial chemistry , acceptor , ring (chemistry) , molecule , stereochemistry , catalysis , organic chemistry , physics , condensed matter physics
A mild and straight‐forward access to pharmacologically privileged tetrahydropyrimidinones exploiting readily available Donor–Acceptor cyclopropanes (DACs) is reported. This methodology involves the Lewis acid catalyzed synthesis of uriedo‐malonates from (un)symmetrical ureas and DACs followed by I 2 ‐base mediated cyclization to their corresponding tetrahydropyrimidinones. The cyclization protocol involves nucleophilic attack of the nitrogen of urea on the newly generated electrophilic acceptor end of DAC. The post functionalization offered potential biologically active molecules.