Studies of seven-membered heterocycles. XXXII. Synthesis of N-unsubstituted 1H-1,4-benzodiazepines stabilized by intramolecular hydrogen bonding
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Sashida,Kaname,Tsuchiya
p. 2919 - 2925
(2007/10/02)
THE FIRST EXAMPLES OF ISOLATED N-UNSUBSTITUTED 1H-1,4-BENZODIAZEPINES
The photolysis in the presence of sodium methoxide of the 4-azidoquinolines (5a-g) having a carbonyl group or its analogue in the 2- or 8-position resulted in ring expansion to give the stable N-unsubstitued 1H-1,4-benzodiazepines (6a-g).These were assumed to be stabilized by intramolecular hydrogen bonding between the NH and the 2- or 9-acyl groups.It is known that the N-unsubstituted 1H-1,4-benzodiazepines having no acyl group are too unstable to be isolated.KEYWORDS---- 4-azidoquinoline; photolysis; ring expansion; N-unsubstituted 1H-1,4-benzodiazepine; hydrogen bonding
Sashida, Haruki,Kaname, Mamoru,Tsuchiya, Takashi
p. 4676 - 4679
(2007/10/02)
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