Synthesis, spectral and structural characterization of isobutyl 4-(2-chlorophenyl)-5-cyano-6-(((dimethylamino)methylene)amino)-2-methyl-4H-pyran-3-carboxylate

• Published in: Journal of molecular structure 2017-09, Vol.1144, p.206-215
• Main Authors: Udhaya Kumar, C., Velayutham Pillai, M., Gokula Krishnan, K., Ramalingan, C.
• Format: Article
• Language: English
• Subjects: Benzene 1,3,5- tricarbonyl trichloride; DFT; Formamidine; FT-Raman; NMR; Single crystal XRD
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2017.05.011

A fascinating selectivity in the direction of the formation of the formamidine was observed upon the reaction of isobutyl 6-amino-4-(2-chlorophenyl)-5-cyano-2-methyl-4H-pyran-3-carboxylate with N,N-dimethyl formamide. A development in selectivity is explored and a probable mechanism for the reaction is also proposed. The formamidine has been analyzed by FT-IR, FT-Raman, LC-MS and NMR (1D and 2D (1H-1H COSY, 1H-13C COSY and HMBC)) spectra. The experimental findings are compared with the theoretical data calculated by using DFT-B3LYP with 6-311++G(d,p) basis set. A good agreement has been observed between experimental and theoretical data. Single crystal X-ray structural analysis of isobutyl 4-(2-chlorophenyl)-5-cyano-6-(((dimethylamino)methylene)amino)-2-methyl-4H-pyran-3-carboxylate (PDMF), evidences the conformation of pyran ring as “flattened−boat”. [Display omitted] •Facile synthesis of formamidine derivative of 4H-pyran.•Spectral characterization by FT-IR, FT-Raman, LC-MS, NMR and HOMO-LUMO band gap investigation by computational method.•Single crystal XRD analysis of isobutyl 4-(2-chlorophenyl)-5-cyano-6-(((dimethylamino)methylene)amino)-2-methyl-4H-pyran-3-carboxylate.