Synthesis of novel quinazolines via nucleophilic cycloaddition of 2-amino-N′-arylbenzimidamides with dimethyl acetylenedicarboxylate and 2-(dicyanomethylene)indan-1,3-dione

Synthesis of novel tetrahydroquinazoline-2-carboxylate and arylaminoquinazoline-2-carboxylate in good yields has been established via the nucleophilic cycloaddition of 2-amino- N ′-arylbenzimidamides on dimethyl acetylenedicarboxylate. Moreover, studying the reaction of 2-amino- N ′-arylbenzimidamid...

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Bibliographic Details
Published in:Monatshefte für Chemie 2019-10, Vol.150 (10), p.1849-1856
Main Authors: Mohamed, Asmaa H., El-Shaieb, Kamal M.
Format: Article
Language:English
Subjects:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Cycloaddition
Inorganic Chemistry
Mass spectra
NMR
Nuclear magnetic resonance
Organic Chemistry
Original Paper
Physical Chemistry
Synthesis
Theoretical and Computational Chemistry
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Summary:Synthesis of novel tetrahydroquinazoline-2-carboxylate and arylaminoquinazoline-2-carboxylate in good yields has been established via the nucleophilic cycloaddition of 2-amino- N ′-arylbenzimidamides on dimethyl acetylenedicarboxylate. Moreover, studying the reaction of 2-amino- N ′-arylbenzimidamides with 2-(dicyanomethylene)indan-1,3-dione to give 3,4-dihydroquinazolin derivatives. The results obtained from IR, 1 H NMR, and 13 C NMR data as well as the mass spectra are in agreement with the assigned structures. A plausible mechanism for the formation of the products is presented. Graphic abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-019-02491-7