Formation of 1, 3-diazocine by palladium catalyzed C–H arylation. Issue 21 (25th May 2016)

• Record Type: Journal Article
• Authors: Tang, Le; Ren, Jing; Ma, Yuchi; Wang, Xin; Chen, Lin; Shen, Jingkang; Chen, Yue-Lei; Xiong, Bing
• Is Part Of: Tetrahedron letters. Volume 57:Issue 21(2016)
• Page Start: 2311
• Page End: 2314
• Publication Date: 2016-05-25
• Subjects: 1, 3-Diazocine -- C–H arylation -- 8-Aminoimidazo[1, 2-a]pyrazines -- 8-Membered ring -- Groebke–Blackburn–Bienaymé reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.04.050
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A DMF-promoted Pd-catalyzed C–H arylation was found. The C–H arylation led to unusual 8-membered ring cyclization. Some rare and valuable 8-membered ( Z )-4, 5-dihydro-3 H -[1, 3]diazocines were prepared. Usage of MCR rendered the preparation of 1, 3-diazocines highly efficient. Abstract: From multi-substituted 8-aminoimidazo[1, 2- a ]pyrazines, prepared via modified Groebke–Blackburn–Bienaymé reaction, a Pd-catalyzed cyclization reaction was discovered, leading to a rare ( Z )-4, 5-dihydro-3 H -[1, 3]diazocine system. Conditions of this cyclization were screened and DMF solvent was found as one of the key factors for the cyclization.