One-pot synthesis of quinoline-fused [1,4]thiazepines via the tandem Ugi/post-Ugi reactions

A one-pot strategy has been developed for the synthesis of novel tetrahydro-[1,4]thiazepino[7,6- b ]quinoline-5-carboxamide derivatives. These reactions presumably proceed by the combination of a Ugi 4CR and three intramolecular S N 2 aliphatic, an alkaline hydrolysis and an intramolecular cyclizati...

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Bibliographic Details
Published in:Journal of the Iranian Chemical Society 2019-02, Vol.16 (2), p.325-332
Main Authors: Ghandi, Mehdi, Efteghar, Irene, Abbasi, Alireza
Format: Article
Language:English
Subjects:
Aliphatic compounds
Analytical Chemistry
Biochemistry
Cascade chemical reactions
Chemical synthesis
Chemistry
Chemistry and Materials Science
Crystal structure
Crystals
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Quinoline
Single crystals
X-ray diffraction
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Summary:A one-pot strategy has been developed for the synthesis of novel tetrahydro-[1,4]thiazepino[7,6- b ]quinoline-5-carboxamide derivatives. These reactions presumably proceed by the combination of a Ugi 4CR and three intramolecular S N 2 aliphatic, an alkaline hydrolysis and an intramolecular cyclization S N Ar nucleophilic substitution processes in moderate to good yields. Unambiguous assignment of the molecular structures was carried out by single-crystal X-ray diffraction.
ISSN:1735-207X
1735-2428
DOI:10.1007/s13738-018-1511-z