Dearomatizing spirocyclization reactions of alkynyl cyanamides. Issue 29 (20th July 2016)

• Record Type: Journal Article
• Authors: Singh, Ravi P.; Spears, Jada A.; Dalipe, Alfonso; Yousufuddin, Muhammed; Lovely, Carl J.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 29(2016)
• Page Start: 3096
• Page End: 3099
• Publication Date: 2016-07-20
• Subjects: Cyanogen bromide -- Cyclohexadienone -- Leucetta alkaloids -- Total synthesis -- Electrophile-induced; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.05.104
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Propargyl amine derivatives undergo dearomatizing spirocyclization. Unusual tandem cyanamidation-bromine-induced dearomatizing spirocyclization. Highly functionalized products and thus represent useful synthons. Abstract: Electrophile-induced dearomatizing spirocyclization reactions of propargylic cyanamides leading to cyclohexadienone derivatives are described. An unusual one-pot spirocyclization-N-cyanation reaction has been discovered leading directly to the spiro fused derivative. The products obtained through this chemistry may serve as key intermediates in synthetic approaches to several Leucetta alkaloids.