Synthesis of cyclopentaquinolinone and cyclopentapyridinone from ortho-alkynyl-N-arylaldehyde via superbase-promoted C–N, C–O and C–C bond formation. Issue 29 (9th July 2020)

• Record Type: Journal Article
• Authors: Saini, Kapil Mohan; Saunthwal, Rakesh K.; Sushmita, ; Verma, Akhilesh K.
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 29(2020)
• Page Start: 5594
• Page End: 5601
• Publication Date: 2020-07-09
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob01281e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An environmentally benign and superbase-mediated intramolecular annulation of o -alkynylaldehydes with primary amines to construct amino-substituted cyclopentaquinolinones and cyclopentapyridinones via C–N, C–C, and CO bond formation is described. Abstract : An environmentally benign, transition metal-free, superbase-mediated intramolecular annulation of o -alkynylaldehydes with primary amines forms highly functionalized amino-substituted cyclopentaquinolinones and cyclopentapyridinones via C–N, C–C, and CO bond formation. Contrary to the traditional approaches of ring closures, a different mode of annulation is disclosed. The protocol involves the in situ generations of imine intermediate followed by potassium hydroxide-promoted intramolecular cyclization and subsequent dimethyl sulfoxide induced dehydrogenation leads to the formation of N-heterocycles. X-ray crystallographic studies support the assigned structures of the amino-fused N-heterocycles.