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Synthesis of New Quinoxaline Derivatives by Reductive Cyclization of Various 1-(2-Nitrophenyl)-2-cyanoamines

✍ Scribed by Tristan Renaud; Jean-Pierre Hurvois; Philippe Uriac

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 401 KB
Volume: 2001
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200103)2001:5<987::aid-ejoc987>3.0.co;2-b

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✦ Synopsis

The electrochemical cyanation of various six-membered N-(2-nitrophenyl) heterocyclic amines, including piperidine, morpholine, thiomorpholine, and N-Boc-protected piperazine derivatives, was investigated. The expected cyanoamines 5 were obtained in good yields and subjected to catalytic hydrogenation to afford the corresponding cyclic amidine Noxides 6. The reductive cyclization proceeded through the formation of a hydroxylamine, which cyclized onto the cyano moiety. The stereoselectivity of the cyclization reaction was [a]

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