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Herein, we reported an effectual protocol for the stereoselective synthesis of novel C-3 thio/seleno substituted  ortho -,  meta - and  para -(2-benzo[ d ]oxazolyl)phenyl-β-lactams  7a-i . The reaction was performed by utilizing different S/Se-alkyl/aryl substituted acids  6a-d  and isomeric  ortho -,  meta - and  para -(2-benzo[ d ]oxazolyl)phenyl Schiff’s bases  3a-c  and afforded exclusive formation of  trans -β-lactams. The  trans  configuration was assigned with respect to coupling constant values of C 3 -H and C 4 -H ( J  = 1.4 to 2.6; C3- H  and C4- H ). The structure elucidation of all the thio/seleno anchored β-lactams  7a-i  was performed using various spectroscopic techniques viz. FT-IR, NMR ( 1 H,  13 C, and  13 C DEPT–135), 2D-NMR ( 1 H– 1 H COSY and  1 H– 13 C HSQC), elemental analysis (CHN), and mass spectrometry (ESI-MS). Further, divergent substrate scope accompanied by plausible mechanistic investigation have been also described. Stereoselectivity, good functional group tolerance and excellent yield along with wider synthetic utility bestows advantages to the present protocol.

journal of sulfur chemistry

Stereoselective synthesis of  trans -benzo[ d ]oxazolyl)phenyl substituted β-lactams decorated with C-3 thio/seleno rich motifs: synthetic intermediates for diverse heterocycles