N. Çolak, A. Karayel, K. Buldurun
Jan 1, 2021
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Journal
Journal of Structural Chemistry
Abstract
Abstract In this work, 6- tert -butyl 3-ethyl 2-amino-4,5-dihydrothieno[2,3-c]pyridine-3,6(7 H )-dicarboxylate is synthesized from starting tert -butyl 4-oxopiperidine-1-carboxylate, ethyl cyanomalonate, and sulfur, and then, coupled with same aromatic aldehyde affords the corresponding Schiff base compounds. These compounds ( 2a–d ) are characterized using FTIR, 1 H and 13 C NMR spectroscopic methods. The crystal and molecular structure of (E)-6- tert -butyl 3-ethyl 2-((2-hydroxy-3-methoxybenzylidene)amino)-4,5-dihydrothieno[2,3-c]pyridine-3,6(7 H )-dicarboxylate ( 2a ) is characterized by the X-ray crystallographic analysis. Compound 2a crystallizes in the monoclinic space group P 2 1 / c . The molecular and crystal structure is stabilized by two O–H⋯N and O–H⋯O intramolecular hydrogen bonds (O⋯N and O⋯O are 2.598(5) Å and 2.990(5) Å, respectively; O–H⋯N = 147° and O–H⋯O = 134°). According to DFT, compound 2d also shows the intramolecular hydrogen bonding, while there is no this type of interaction in compound 2b and 2c .