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Paper | Regular issue | Vol 96, No. 5, 2018, pp.839-849
Published online, 26th April, 2018
DOI: 10.3987/COM-17-13796
■ Solvent-Free Microwave Accelerated Synthesis and Structural Characterization of Phthalide-Fused Indolines

Wong Sheryn, Fatimatul Akma Awang Ngah, Jalifah Latip, Nurul Izzaty Hassan, and Siti Aishah Hasbullah*

*School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia

Abstract

The 3-substituted phthalides (3a–3d) were synthesized by coupling reaction of methylenindoline derivatives (1) with 2-formylbenzoic acid derivatives (2), under solvent-free microwave irradiation. The reaction rate enhancement resulted from irradiation has proven to be higher and more efficient compared to the conventional method with an excellent yield of 80–98%. The structures of the phthalides were deduced by their analytical and spectral data (FTIR, UV-Vis, 1H NMR, 13C NMR, LC-MS) and confirmed by chemical crystallography. Compounds 3a and 3b were successfully crystallized in monoclinic system with space group P21/c and C2/c, respectively. The molecular structure consists of fused 1 and 2 groups connected by the enamine carbon.