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Dihydroquinazolino[3,2‐ a ][1,5]benzodiazepines: Synthesis and Computational Study of Reductive N‐Heterocyclization of N ‐(2‐Nitrobenzoyl)‐1,5‐benzodiazepin‐2‐ones
Author(s) -
Janciene Regina,
Mikulskiene Gema,
Javorskis Tomas,
Vektariene Ausra,
Vektaris Gytis,
Kosychova Lidija
Publication year - 2015
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.2038
Subject(s) - chemistry , hydroxylamine , reactivity (psychology) , quantum chemical , chloride , medicinal chemistry , combinatorial chemistry , organic chemistry , molecule , medicine , alternative medicine , pathology
A number of 6,7‐dihydroquinazolino[3,2‐ a ][1,5]benzodiazepin‐13(5 H )‐ones were prepared utilizing the coupling of readily available 5‐acyl‐1,3,4,5‐tetrahydro‐2 H ‐1,5‐benzodiazepin‐2‐ones with 2‐nitrobenzoyl chloride followed by a reductive N‐heterocyclization. 3‐Methylsubstituted 1‐(2‐nitrobenzoyl)‐1,5‐benzodiazepinone derivatives did not cyclize under the reductive N‐heterocyclization conditions. The possible mechanism of this heterocyclization was discussed, and it was demonstrated that the hydroxylamine intermediate was the initiator of this reaction. To clarify the reasons of different reactivities of various 1,5‐benzodiazepine derivatives, the quantum‐chemical reactivity descriptors of the hydroxylamine intermediates were calculated and evaluated.