Synthesis of diazabicyclo compounds possessing an α-nitrolactam framework. Issue 19 (6th May 2015)

• Record Type: Journal Article
• Authors: Asahara, Haruyasu; Takeda, Shota; Saigo, Kazuhiko; Nishiwaki, Nagatoshi
• Is Part Of: Tetrahedron letters. Volume 56:Issue 19(2015)
• Page Start: 2504
• Page End: 2507
• Publication Date: 2015-05-06
• Subjects: Bicyclic compound -- Michael addition -- Nitroacetate -- Pseudo-intramolecular process; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.03.100
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Diazabicyclo compounds possessing an α-nitrolactam framework were directly synthesized upon treatment of α-nitro-δ-keto esters with diamines. This reaction proceeds via pseudo-intramolecular process. In this process, the formation of ammonium nitronate is a key step, by which the amino group and the ketone carbonyl group are in close proximity to cause the imine formation efficiently. The following tandem bicyclization constructs 1, 7-diaza-3-nitro-2-oxobicyclic systems having two aryl groups at the 4- and 6-positions.