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- Title
The Synthesis of New Heterocycles Using 2-(4-Chloro-1,3-dihydro-3,3,7-trimethyl-2 H-indol-2-ylidene) Propanedial.
- Authors
Alyari, Maryam; Baradarani, Mehdi M.; Afghan, Arash; Joule, John A.
- Abstract
4-Chloro-2,3,3,7-tetramethyl-3 H-indole (an indolenine) was produced by the reaction of 5-chloro-2-methylphenylhydrazine hydrochloride with 3-methylbutan-2-one via Fischer reaction. Exposure of the indolenine to the Vilsmeier reagent at 50°C produced a β-diformyl compound, 2-(4-chloro-1,3-dihydro-3,3,7-trimethyl-2 H-indol-2-ylidene)propanedial. This dialdehyde was reacted with arylhydrazines, acetamidinium chloride, urea, thiourea, guanidinium chloride, and cyanoacetamide to give various 5-membered and 6-membered heterocyclic products, each carrying a 4-chloro-3,3,7-trimethyl-3 H-indol-2-yl unit as a substituent, in excellent yields.
- Subjects
HETEROCYCLIC compounds synthesis; INDOLE; PHENYLHYDRAZINE; ISOPENTANE; VILSMEIER reagents; ALDEHYDES; UREA; GUANIDINIUM chlorides
- Publication
Journal of Heterocyclic Chemistry, 2014, Vol 51, Issue 3, p854
- ISSN
0022-152X
- Publication type
Article
- DOI
10.1002/jhet.1626