Synthesis, characterization, thermal, X-ray, and DFT analyses of 6-tert-butyl 3-ethyl 2-[(3-methoxy/5-bromo)-2-hydroxy and (3-nitro/3-methoxy)benzylideneamino]-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylate

doi:10.26902/jsc_id68309

Paper

Synthesis, characterization, thermal, X-ray, and DFT analyses of 6-tert-butyl 3-ethyl 2-[(3-methoxy/5-bromo)-2-hydroxy and (3-nitro/3-methoxy)benzylideneamino]-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylate

Published 2021 · N. Çolak, A. Karayel, K. Buldurun

Журнал структурной химии

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Abstract

In this work, 6-tert-butyl 3-ethyl 2-amino-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-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, 1H and 13C 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(7H)-dicarboxylate (2a) is characterized by the X-ray crystallographic analysis. Compound 2a crystallizes in the monoclinic space group P21/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.

Study Snapshot

This study successfully synthesized 6-tert-butyl 3-ethyl 2-((2-hydroxy-3-methoxybenzylidene)amino)-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylate,

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis, characterization, thermal, X-ray, and DFT analyses of 6-tert-butyl 3-ethyl 2-[(3-methoxy/5-bromo)-2-hydroxy and (3-nitro/3-methoxy)benzylideneamino]-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylate

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