Synthesis of fluorescent heterocycles via a Knoevenagel/[4 + 1]-cycloaddition cascade using acetyl cyanide. Issue 29 (7th July 2017)

• Record Type: Journal Article
• Authors: Martinez-Ariza, Guillermo; Mehari, Bereketab T.; Pinho, Ludmila A. G.; Foley, Christopher; Day, Kendall; Jewett, John C.; Hulme, Christopher
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 29(2017)
• Page Start: 6076
• Page End: 6079
• Publication Date: 2017-07-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob01239j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Acetyl cyanide is utilized to synthesize fluorescent indolizines, benzo[ d ]pyrrolo[2, 1- b ]thiazoles, and pyrrolo[1, 2- a ]pyrazines in a single step. Abstract : A concise one-pot three-component reaction that affords fluorescent indolizines, benzo[ d ]pyrrolo[2, 1- b ]thiazoles, and pyrrolo[1, 2- a ]pyrazines is reported. The methodology involves the formation of a heterocyclic 1-aza-1, 3-diene derived from a Knoevenagel condensation between an aldehyde and 2-methyl-ene-cyano aza-heterocycles, followed by [4 + 1] cycloaddition of acetyl cyanide behaving as a non-classical isocyanide replacement.