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Synthesis of naphtho[1,2‐ b ]‐, naphtho[2,1‐ b ]‐, and naphtho[2,3‐ b ]azepinones via proton‐induced cyclization of N ‐1(2)‐naphthyl styrylacetamides
Author(s) -
Danyliuk Ivanna Y.,
Vaskevych Ruslan I.,
Vaskevych Alla I.,
Suikov Sergii Y.,
Rusanov Eduard B.,
Chornous Vitalij O.,
Vovk Mykhailo V.
Publication year - 2020
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.3779
Subject(s) - chemistry , ring (chemistry) , aryl , amide , stereochemistry , nitrogen atom , intramolecular force , medicinal chemistry , organic chemistry , alkyl
On heating in polyphosphoric acid, N ‐1‐naphthyl styrylacetamides undergo proton‐induced intramolecular cyclization at position 2 of the naphthyl ring to provide 5‐aryl‐1,3,4,5‐tetrahydro‐2 Н ‐naphtho[1,2‐ b ]azepin‐2‐ones, while their N ‐2‐naphthyl analogues, when similarly reacted, are cyclized at positions 1 and 3 of the naphthyl ring and at the amide nitrogen atom leading, respectively, to 1‐aryl‐1,2,3,5‐tetrahydro‐4 Н ‐naphtho[2,1‐ b ]azepin‐4‐ones, 5‐aryl‐1,3,4,5‐tetrahydro‐2 Н ‐naphtho[2,3‐ b ]azepin‐2‐ones, and 5‐aryl‐1‐(2‐naphthyl)pyrrolidin‐2‐ones.