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Updated: May 20, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
8-Methyl-2-oxo-4-(thio-phen-2-yl)-1,2,5,6,7,8-hexa-hydro-quinoline-3-carbonitrile
Abstract:
In the title compound, C(15)H(14)N(2)OS, the pyridinone ring in the fused-ring system is nearly planar (r.m.s. deviation = 0.011 Å) and the cyclo-hexene ring has a twisted half-boat conformation with the methyl-ene C atom adjacent to the methine C atom deviating by 0.592 (7) Å from the plane defined by the remaining five atoms (r.m.s. deviation = 0.108 Å). The thienyl ring is disordered over two almost coplanar positions of opposite orientation in a 0.649 (4):0.351 (4) ratio, and forms dihedral angles of 51.4 (3) (major component) and 54.2 (3)°, respectively, with the pyridinone ring. In the crystal, inversion-related mol-ecules associate via an eight-membered {⋯HNCO}(2) synthon and these are linked into a linear supra-molecular chain along the a axis by weak π-π inter-actions that occur between centrosymmetrically related pyridinone rings [centroid-centroid distance = 3.889 (2) Å].
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