n N → π Ar interactions stabilize the E -ac isomers of arylhydrazides and facilitate their S N Ar autocyclizations

We describe a novel mechanism of stabilization of the E -ac isomer of an arylhydrazide via n N → π* Ar interactions. We further show that when a leaving group (F) is present at the ortho -position of the carbonyl group of such an arylhydrazide, the n N → π* Ar interaction facilitates an S N Ar autoc...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-10, Vol.57 (85), p.11236-11239
Main Authors: Deka, Jugal Kishore Rai, Kalita, Debajit, Sahariah, Biswajit, Sarma, Bani Kanta
Format: Article
Language:English
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Summary:We describe a novel mechanism of stabilization of the E -ac isomer of an arylhydrazide via n N → π* Ar interactions. We further show that when a leaving group (F) is present at the ortho -position of the carbonyl group of such an arylhydrazide, the n N → π* Ar interaction facilitates an S N Ar autocyclization reaction to produce indazolone, an important heterocycle with biological activity. Faster autocyclization of arylhydrazide is observed when an electron withdrawing group is present in the aryl ring, which is a characteristic of S N Ar reactions.
ISSN:1359-7345
1364-548X
DOI:10.1039/D1CC04533D