Lewis acid-promoted synthesis of highly substituted pyrrole-fused benzoxazinones and quinoxalinones. Issue 3 (1st February 2021)

• Record Type: Journal Article
• Authors: Selvendran, Suresh; Rajendran, Saravanakumar
• Is Part Of: Synthetic communications. Volume 51:Issue 3(2021)
• Page Start: 437
• Page End: 445
• Publication Date: 2021-02-01
• Subjects: Benzoxazinone -- oxindole -- pyrrole -- quinoxalinones -- tin(IV) chloride; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2020.1832528
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: A synthesis of a series of novel fused tricyclic heterocyclic compounds has been achieved in one-pot reaction set up starting from ( E )-3-(2-oxo-2-phenylethylidene)indolin-2-one and 1, 4-benzoxazinone/quinoxalinone derivatives promoted by tin(IV) chloride. The reaction is supposed to occur via a sequential intermolecular Michael addition of the 1, 4-benzoxazinone derivatives to the oxindoles, intramolecular cyclization, and aromatization with the elimination of water. Apart from spectroscopic characterization, the structure of one of the pyrrolo[1, 4]benzoxazinone derivative is confirmed by single-crystal X-ray diffraction. Thus, the developed domino protocol provides easy access to multifunctional pyrrolo[1, 4]benzoxazines in one-pot with high efficiency. Graphical Abstract: