3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carboxylic acid
نویسندگان
چکیده
The title mol-ecule, C(14)H(19)NO(6), was synthesized by the reaction of glyoxylic acid, ethyl acetoacetate and NH(4)HCO(3). In the crystal structure, the dihydro-pyridine ring adopts an asymmetric boat-type conformation with the C atom bearing the carboxyl group showing a signficantly larger deviation [0.325 (2) Å] from the base plane then the N atom [0.137 (2) Å]. One of the ethyl groups is disordered over two positions with occupancies of 0.741 (10) and 0.259 (10). The crystal is stabilized by strong inter-molecular hydrogen bonds. N-H⋯O inter-actions form infinite chains in the a direction. O-H⋯O hydrogen bonds form typical carboxylic acid dimers, which link the N-H⋯O chains into a ladder-type double chain.
منابع مشابه
Hantzsch synthesis of 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(o-methoxyphenyl)-1,4-dihydropyridine; a novel cyclisation leading to an unusual formation of 1-amino-2-methoxy-carbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene.
Hantzsch condensation of two equivalents of methyl-3-aminocrotonate with (m- and p)-methoxybenzaldehyde afforded the expected products 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(m-methoxyphenyl)-1,4-dihydropyridine and 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(p-methoxyphenyl)-1,4-dihydropyridine, whereas o-methoxy-benzaldehyde produced mainly 1-amino-2-methoxycarbonyl-3,5-bis(o-methoxy-phenyl)-4-oxa-cy...
متن کاملDiethyl 2,6-dimethyl-4-[5-(4-methylphenyl)-1H-pyrazol-4-yl]-1,4-dihydropyridine-3,5-dicarboxylate
In the title compound, C23H27N3O4, the dihydro-pyridine ring adopts a (1,4)B conformation. Intra-molecular C-H⋯O contacts occur. In the crystal, N-H⋯O and N-H⋯N hydrogen bonds and C-H⋯N contacts connect the mol-ecules into strands along the a-axis direction.
متن کاملDiethyl 2,6-dimethyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylate
In the title compound, C(20)H(25)NO(4), the 1,4-dihydro-pyridine ring adopts a flattened-boat conformation and forms a dihedral angle of 89.77 (8)° with the benzene ring. Inter-molecular N-H⋯O hydrogen bonds result in the formation of extended chains parallel to the b axis.
متن کامل4-[3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-4-pyridyl]pyridinium nitrate
In the title mol-ecular salt, C(18)H(21)N(2)O(4) (+)·NO(3) (-), the dihedral angle between the two pyridine rings is 61.24 (8)°. In the crystal, the cation and anion are linked by inter-molecular N-H⋯O hydrogen bonds.
متن کاملDimethyl 2,6-dimethyl-4-(3-phenyl-1H-pyrazol-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate
In the title compound, C(20)H(21)N(3)O(4), the 1,4-dihydro-pyridine ring adopts a boat conformation. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The pyrazole ring makes dihedral angles of 87.81 (7) and 45.09 (7)° with the mean plane of the 1,4-dihydro-pyridine ring and the phenyl ring, respectively. In the crystal, mol-ecules are linked by N-H⋯N, N-H⋯O and C-H⋯O hydroge...
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عنوان ژورنال:
دوره 65 شماره
صفحات -
تاریخ انتشار 2009