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Stereoselective Synthesis of Novel Monocyclic cis‐β‐Lactams Bearing 1,3,4‐Thiadiazole Nucleus: Bioactive Agents and Potential Synthons
Author(s) -
Mishra Mahesh Kumar,
Sharma Sitaram,
Ahmad Khursheed,
Singh Vedeshwar Narayan
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202000552
Subject(s) - synthon , chemistry , ketene , stereoselectivity , cycloaddition , tetralone , borane , proton nmr , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
A simple and efficient procedure for the stereoselective synthesis of novel monocyclic cis‐ β‐lactams, pharmaceutically fascinating and potential synthons have been developed. The reaction of ketene derived insitu from phenoxyacetyl chloride with tetralone substituted imines resulted in the exclusive formation of monocyclic cis‐ β‐lactams containing 1,3,4‐thiadiazole nucleus by [2+2] cycloaddition reaction. The structures of all the novel synthesized monocyclic cis ‐β‐lactams were verified using various spectroscopic techniques such as FT‐IR, 1 H NMR, 13 C NMR, HRMS, and elemental analysis (CHN). The cis configuration of β‐lactams was deduced using the coupling constant (J) value of H‐3 and H‐4. The prominent features of this work are simple reaction conditions, good yields, easy isolation of products, and no column chromatography separation. All products were obtained by a simple crystallization technique.