Transition metal free intramolecular approach for the synthesis of cyclopenta[b]chromene derivatives from phenol substituted fulvene derived azabicyclic olefins. Issue 27 (6th July 2016)

• Record Type: Journal Article
• Authors: Vijayan, Ajesh; Baiju, T.V.; Varughese, Sunil; Radhakrishnan, K.V.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 27/28(2016)
• Page Start: 2965
• Page End: 2968
• Publication Date: 2016-07-06
• Subjects: 2H-Chromene -- Base catalyzed -- Pentafulvene -- Diazabicyclic olefin -- Electrocyclic ring closure; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.05.081
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Synthesis of cyclopenta[ b ]chromene derivatives from diazabicyclic olefins. Reaction proceeds via base-catalyzed intramolecular ring opening and ring closure. The mechanism is proposed via zwitter ion or electrocyclic ring closure pathway. Easy access to biologically relevant systems under mild reaction conditions. Abstract: A facile route towards the synthesis of cyclopentene fused chromene derivatives from strained phenol substituted fulvene derived bicyclic hydrazines is described. The reaction is proceeding through base catalyzed sequential intramolecular ring opening and ring closure of azabicyclic olefins. The transition metal free method provides an easy access to biologically relevant fused chromene ring system under relatively mild reaction conditions.