An Efficient and Concise Synthesis of N-3-Substituted 9-Methoxy-4 H -[1]-benzopyrano[2,3- d ]pyrimidine-4(5 H)-imines and Formamidine Derivatives from Methyl N -(3-Cyano-8-methoxy-4 H -[1]-benzopyran-2-yl)methanimidate

A. Bouattour , M. Fakhfakh , S. Abid , L. Paquin (1, 2) , H. Ammar , J.-P. Bazureau (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 ScanMAT - Synthèse Caractérisation Analyse de la Matière

A four-step microwave-assisted reaction of N-3-susbstituted 4 H -[1]-benzopyrano[2,3- d ]pyrimidine-4(5 H)-imines and formamidine derivatives was successfully developed from primary amines, cyclic secondary amines, and methyl N -(3-cyano-8-methoxy-4 H -[1]-benzopyran-2-yl)methanimidate as key intermediate. The simplicity of the microwave protocols gave facile possibilities of isolation of the desired products by simple filtration. The synthesized compounds were obtained in good yields and purity, and characterized by 1 H, 13 C NMR, IR, and HRMS analyses. © Georg Thieme Verlag Stuttgart - New York.

Keywords: (benzopyran-2-yl)methanimidate; benzopyranopyrimidine-4-imine; formamidine; microwave irradiation; solvent-free

Domains: Chemical Sciences

A. Bouattour, M. Fakhfakh, S. Abid, L. Paquin, H. Ammar, et al.. An Efficient and Concise Synthesis of N-3-Substituted 9-Methoxy-4 H -[1]-benzopyrano[2,3- d ]pyrimidine-4(5 H)-imines and Formamidine Derivatives from Methyl N -(3-Cyano-8-methoxy-4 H -[1]-benzopyran-2-yl)methanimidate. Synthesis: Journal of Synthetic Organic Chemistry, 2017, 49 (16), pp.3768--3774. ⟨10.1055/s-0036-1588825⟩. ⟨hal-01581228⟩