A study on the reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines with ninhydrin

Autor:	Mustafa M. El-Abadelah, Wolfgang Voelter, Salim S. Sabri, Firas F. Awwadi, Mervat S. Sammor, Ahmad Q. Hussein
Rok vydání:	2018
Předmět:	chemistry.chemical_classification Electrophilic substitution chemistry.chemical_compound 010405 organic chemistry Chemistry Aryl Ninhydrin Organic chemistry General Chemistry 010402 general chemistry 01 natural sciences Alkyl 0104 chemical sciences
Zdroj:	Zeitschrift für Naturforschung B. 73:413-421
ISSN:	1865-7117 0932-0776
DOI:	10.1515/znb-2018-0039
Popis:	The reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines (1) with ninhydrin in dichloromethane at room temperature delivered good yields of the respective 2-hydroxy-2-(imidazo[1,5-a]pyridine-1-yl)indene-1,3-diones. In the presence of dimethyl acetylenedicarboxylate (DMAD), this uncatalyzed electrophilic substitution reaction, involving C-1 (in 1) and the central C=O (in ninhydrin), takes precedence over the three-component 1,4-dipolar cycloaddition reaction. This selectivity is probably due to the higher electrophilicity of the carbonyl carbon-2 in ninhydrin as compared to that of the sp-carbon atoms in DMAD, augmented with the high nucleophilicity of carbon-1 in 1.
Databáze:	OpenAIRE
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