Practical synthesis of 3, 3-substituted dihydroquinoxalin-2-ones from aryl 1, 2-diamines using the Bargellini reaction. Issue 39 (28th September 2016)

• Record Type: Journal Article
• Authors: Alanine, Thomas A.; Stokes, Stephen; Scott, James S.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 39(2016)
• Page Start: 4386
• Page End: 4388
• Publication Date: 2016-09-28
• Subjects: Dihydroquinoxalin-2-one -- Bargellini reaction -- Trichloromethylcarbinol -- Synthetic methodology -- Heterocyclic synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.08.057
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Provides access to useful 3, 3-disubstituted dihydroquinoxalinones in good yields. The mild reaction conditions tolerate a variety of chemical functionalities. Complexity is readily incorporated on the saturated ring. Pyridine diamines can be used as well as o -phenylene diamines. The formation of regioisomers is rationalised mechanistically. Abstract: The reaction of aromatic 1, 2-diamines with trichloromethylcarbinols under mild, basic phase-transfer conditions provided expedient access to 3, 3-disubsituted quinoxalin-2(1 H )-ones in good to moderate yields. The use of unsymmetrical aryl diamines gave a regioisomeric mixture of products with the ratio shown to be dependent on the electronic nature of the aromatic substituents. 2, 3-Diaminopyridines could also be used, showing excellent selectivity for the dihydro[3, 2- b ]pyridopyrazin-2-one isomer.