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Synthesis of α‐diaminomethylenebutyrolactams by the reaction of α‐cyanobutyrolactams with n ‐trimethylsilylamines
Author(s) -
Okabe Fumi,
Nakamura Syouhei,
Yamagata Kenji
Publication year - 2007
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570440137
Subject(s) - chemistry , dimethylamine , morpholine , pyrrolidine , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , medicinal chemistry , organic chemistry
uccessive treatment of α‐cyanobutyrolactams 1 with N ‐trimethylsilylamines and water gave the corresponding α‐diaminomethylenebutyrolacatms 2 in good yields. In the NOESY spectra of 2 , the E isomer, the NOE observed between β‐CH 2 (butyrolactam) and N ‐CH 2 (morpholine, pyrrolidine) or N ‐CH 3 (dimethylamine) indicated a cis configuration of these groups.