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The Synthesis of New Heterocycles Using 2‐(4‐Chloro‐1,3‐dihydro‐3,3,7‐trimethyl‐2 H ‐indol‐2‐ylidene) Propanedial
Author(s) -
Alyari Maryam,
Baradarani Mehdi M.,
Afghan Arash,
Joule John A.
Publication year - 2014
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.1626
Subject(s) - chemistry , thiourea , reagent , chloride , hydrochloride , indole test , substituent , medicinal chemistry , urea , cyanoacetamide , organic chemistry
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.