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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Tarih
2021
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Pleiades Publishing Inc
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
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, H-1 and C-13 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 P2(1)/c. The molecular and crystal structure is stabilized by two O-HMIDLINE HORIZONTAL ELLIPSISN and O-HMIDLINE HORIZONTAL ELLIPSISO intramolecular hydrogen bonds (OMIDLINE HORIZONTAL ELLIPSISN and OMIDLINE HORIZONTAL ELLIPSISO are 2.598(5) angstrom and 2.990(5) angstrom, respectively; O-HMIDLINE HORIZONTAL ELLIPSISN = 147 degrees and O-HMIDLINE HORIZONTAL ELLIPSISO = 134 degrees). According to DFT, compound 2d also shows the intramolecular hydrogen bonding, while there is no this type of interaction in compound 2b and 2c.
Açıklama
Anahtar Kelimeler
heterocyclic amine, Schiff base, DFT, X-ray
Kaynak
Journal Of Structural Chemistry
WoS Q Değeri
Q4
Scopus Q Değeri
Q3
Cilt
62
Sayı
1
