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

• Published in: Monatshefte für Chemie Vol. 150; no. 10; pp. 1849 - 1856
• Main Authors: Mohamed, Asmaa H., El-Shaieb, Kamal M.
• Format: Journal Article
• Language: English
• Published: Vienna Springer Vienna 01.10.2019; Springer Nature; Springer Nature B.V
• Subjects: Analytical Chemistry; Chemistry; Chemistry and Materials Science; Chemistry, Multidisciplinary; Chemistry/Food Science; Cycloaddition; Inorganic Chemistry; Mass spectra; NMR; Nuclear magnetic resonance; Organic Chemistry; Original Paper; Physical Chemistry; Physical Sciences; Science & Technology; Synthesis; Theoretical and Computational Chemistry; arylbenzimidamides; Dimethyl acetylenedicarboxylate; 2-Amino; 2-(Dicyanomethylene)indan-1,3-dione; Quinazolines; 2-Amino-N '-arylbenzimidamides; DERIVATIVES
• ISSN: 0026-9247; 1434-4475
• DOI: 10.1007/s00706-019-02491-7

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