Synthesis and absolute configuration of methyl (–)-(3R)-8-(4-bromophenyl)-7-(naphthalen-1-ylmethyl)-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridine-3-carboxylate

Abstract

The title mol­ecule, C26H20BrNO3S, contains a ring‐fused 2‐pyridinone framework substituted with a 4‐bromo‐phenyl‐, a naphthalen‐1‐yl­methyl and a methoxy­carbonyl substituent. The main goal of this work was to confirm the stereochemistry for the methoxy­carbonyl substituent, which proved to be 3R. Moreover, the 4‐bromo­phenyl substituent was shown to be rotated out of the plane of the 2‐pyridinone ring, with a torsion angle of 61.2 (5)°. To allow the best packing arrangement, the naphthalen‐1‐yl­methyl substituent is pos­itioned to mediate an intermolecular π–π interaction.

Crystal Growth, Single Crystal Structure, and Biological Activity of Thiazolo-Pyridine Dicarboxylic Acid Derivatives

“…The interatomic S1-C1 and S1-C7 distances that vary from 1.810 (3) Å to 1.821 (2) Å and from 1.734 (2) Å to 1.750 (2) are typical of the S-Csp 3 and S-Csp 2 bonds, respectively. 11,22,23,26 The bond configurations at the N1 atoms are planar trigonal with the sum of the N1 bond angles almost 360°. The bicyclic S1N1C2-C8 systems can be regarded as planar since the dihedral angles between the sixand five-membered rings are less than 11°.…”

“…The interatomic S1-C1 and S1-C7 distances of 1.810 (3) Å and 1.734 (2) Å are typical of the S-Csp 3 and S-Csp 2 bonds, respectively. 11,22,23 The bicyclic S1N1C2-C8 system can be regarded as planar since the dihedral angle between the sixand five-membered rings is only 4.01°. The carboxyl group C8O2O3H is almost co-planar with the bicyclic fragment with a dihedral angle of 6.01°.…”

“…The puckering parameters Q = 0.226 (2) Å and φ = 43.2 (5)° and the pseudorotation parameters P = 212.6 (3)° and Tau­( M ) = 22.2 (1)° for the reference bond S1-C1 suggest an envelope conformation on C1. The interatomic S1-C1 and S1-C7 distances of 1.810 (3) Å and 1.734 (2) Å are typical of the S-Csp 3 and S-Csp 2 bonds, respectively. ,, The bicyclic S1N1C2-C8 system can be regarded as planar since the dihedral angle between the six- and five-membered rings is only 4.01°. The carboxyl group C8O2O3H is almost co-planar with the bicyclic fragment with a dihedral angle of 6.01°.…”