Facile synthesis of novel benzothiazolylpyrazolyl anchored 3-thio/seleno/chloro-β-lactams: Synthetic intermediates for novel 3-sulfenyl/sulfonyl, C-3 functionalized monocyclic and spirocyclic β-lactams. Issue 20 (18th October 2018)

• Record Type: Journal Article
• Authors: Bhalla, Jitender; Bari, Shamsher S.; Bhalla, Aman
• Is Part Of: Synthetic communications. Volume 48:Issue 20(2018)
• Page Start: 2675
• Page End: 2682
• Publication Date: 2018-10-18
• Subjects: benzothiazole -- phenyl/benzylthio -- pyrazole -- trans-β-lactams; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2018.1515366
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: Efficient synthesis of a new series of 3-phenyl/benzylthio-4-benzothiazolylpyrazolyl-β-lactams is described. Treatment of 2-phenylthio/benzylthioacetic acid with benzothiazolylpyrazolyl substituted Schiff's bases furnished trans-β-lactams exclusively. Newly synthesized substituted Schiff's bases and β-lactams were identified using FT-IR, 1 H NMR, 13 C NMR and elemental analysis (CHN). The trans configuration was assigned with respect to coupling constant values of C3-H and C4-H. The novel β-lactams will be the potential synthetic intermediates to access 3-sulfenyl/sulfonyl, C-3 functionalized monocyclic and spirocyclic β-lactams of medicinal interest. The present manuscript provides first report on β-lactams linked to bulky group benzothiazolylpyrazolyl. Graphical Abstract: