(±)-trans-6,7-Dimethoxy-1-oxo-3-(2-thienyl)isochroman-4-carboxylic acid
نویسندگان
چکیده
The title compound, C(16)H(14)O(6)S, was synthesized by the reaction of 6,7-dimethoxy-homophthalic anhydride with thio-phene-2-carbaldehyde in the presence of 4-(dimethyl-amino)pyridine (DMAP) as a basic catalyst. The thio-phene ring of the title mol-ecule is disordered over two sites with occupancies of 0.877 (3) and 0.123 (3). The disorder corresponds to an approximate 180° rotation of the thio-phene ring with respect to the C-C bond linking it to the rest of the mol-ecule. The six-membered ring of the 3,4-dihydro-isochromanone ring system is not planar [puckering parameters Q(T) = 0.571 (2) Å, θ = 115.2 (2)° and ϕ = 99.1 (2)°]. The benzene ring of the 3,4-dihydro-isochromanone ring system makes dihedral angles of 75.0 (2) and 77.2 (5)° with the disordered thio-phene rings. Inter-molecular O-H⋯O and C-H⋯O hydrogen bonds, as well as C-H⋯π inter-actions, lead to the observed supra-molecular structure.
منابع مشابه
Synthesis and biological properties of Enantiomers of 1-Allyl-4-Hydroxy-6,7-Dimethoxy-2-Oxo-1,2- Dihydroquinoline-3-Carboxylic Acid (1-Ethylpyrrolidin- 2-Ylmethyl)-Amide Hydrochloride
Being guided by the methodological principles of "chiral switches", the synthesis of Sand Renantiomers of 1-allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (1ethylpyrrolidin-2-ylmethyl)-amide hydrochloride has been carried out. According to the results of the biological research, it has been found that the ability of the optical isomers obtained to block opioid recept...
متن کاملMethyl trans-rac-2-hexyl-1-oxo-3-(2-pyridyl)-1,2,3,4-tetrahydroisoquinoline-4-carboxylate
The title compound, C(22)H(26)N(2)O(3), was synthesized by esterification of trans-rac-2-hexyl-1-oxo-3-(2-pyrid-yl)-1,2,3,4-tetra-hydro-isoquinoline-4-carboxylic acid in the presence of H(2)SO(4) in methanol. The dihedral angle between the benzene and pyridine rings is 84.46 (17)°. The piperidine ring adopts a screw-boat conformation. In the crystal, inversion dimers linked by two C-H⋯O bonds o...
متن کاملSynthesis, antibacterial and antifungal activities of some newer cephlosporin derivatives
7-(D-5-Amino-5-carboxy-valeramido)-3-(acetylhydrazido)-8-oxo-5-thio-1-azabicyclo [4,2,0]-oct2-ene-2-carboxylic acid (1). 7-(D-5-Amino-5-carboxy-valeramido)-3-(substitutedarylacetylhydrazido)8-oxo-5-thio-1-azabicyclo[4,2,0]-oct-2-ene-2-carboxylic acid.(2-5). 7-(D-5Amino-5carboxyvaleramido)3(2'substituted aryl-3'-chloro-4'-oxo-azetidin-1'-yl)-acetylamino]-8-oxo-5-thio-1azabicyclo[4,2,0]-oct-2-ene...
متن کاملSynthesis and Antimicrobial Studies of Biphenyl-4- Carboxylic Acid 2-(aryl)-4-oxo-thiazolidin-3-yl – Amide
Some derivatives of biphenyl-4-carboxylic acid 2-(aryl)-4-oxo-thiazolidin-3-yl –amide were synthesized and studied for their antimicrobial activity. These compounds were prepared from biphenyl-4-carboxylic-acid hydrazides. Biphenyl-4-carboxylic-acid hydrazides 1 on refluxing with aryl aldehydes in the presence of catalytic amount of glacial acetic acid furnish the biphenyl-4-carboxylic acid hyd...
متن کاملOptical Resolution of 5-Oxo-1-phenyl-pyrazolidine-3-carboxylic Acid as a New Organocatalyst for Organic Reactions
Optical resolution of racemic 5-oxo-1-phenyl-pyrazolidine-3-carboxylic acid 2 with L-amino acid methyl ester via the diastereomers formation was investigated. Treatment of racemic 5-oxo-1-phenylpyrazolidine-3-carboxylic acid 2 with L-valine methyl ester gave diastereomers with a total yield of 86%. The diastereomeric dipeptides can be easily separated by flash column chromatography. Acidic clea...
متن کامل