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

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.

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Funding

The authors acknowledge the Aksaray University Science and Technology Application and Research Center, Aksaray, Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010K120480 of the State of Planning Organization). The numerical calculations reported in this paper were fully performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).

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Çolak, N., Karayel, A., Buldurun, K. et al. 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. J Struct Chem 62, 37–46 (2021). https://doi.org/10.1134/S0022476621010054

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Keywords

  • heterocyclic amine
  • Schiff base
  • DFT
  • X-ray.