Formation and Cleavage of N-(Benzenesulfonyl)ethylenimines

Gensler, Walter J.; Brooks, Baruch; Koehler, W

doi:10.1021/jo01023a535

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Synthesis of 6‐amino‐1‐benzyl‐4‐methylhexahydro‐1H‐1,4‐diazepine

Kato

Harada

Morie

1995

Journal of Heterocyclic Chem

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Five variants (methods A—E) of a synthetic route to 6‐amino‐1‐benzyl‐4‐methylhexahydro‐1H‐1,4‐diazepine (3b) using N‐benzyl‐N'‐methylethylenediamine (8a) are described. The reaction of 8a with 1‐benzenesulfonyl‐2‐bromomethylaziridine (7), 2‐phenyl‐4‐(p‐toluenesulfonyloxymethyl)oxazoline (13), and β, β‐dibromoisobutyric acid (15) resulted in the direct cyclization to give the precursor of 3b, 6‐substituted 1,4‐diazepine derivatives 9, 14, and 16, respectively (methods A—C). These compounds were transformed into the desired 3b, The preparation of 1,4‐diazepine ring from methyl 2‐tert‐butoxycarbonyl‐aminopropenate (18) was alternatively achieved by the intramolecular amidation of the intermediate 19a (method D) or reductive cyclization of the aminoaldehyde 23a (method E). Method E was found to efficiently produce the 6‐amino‐1,4‐diazepine 3b.

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