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Synthesis of Bis(trifluoromethylated) Pyrazine-containing Nitrogen Heterocycles from Hexafluorobiacetyl and ortho-Diamines. Stabilization of the Covalent Dihydrates of Pteridines and Pyridopyrazines by Trifluoromethyl Groups

DOI: 10.1039/P19860001043

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1043 - 1050 (1986)

Update date:2022-07-29

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Authors:

Cushman, MarkCushman, Mark

Wong, Wai CheongWong, Wai Cheong

Bacher, AdelbertBacher, Adelbert

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Article abstract of DOI:10.1039/P19860001043

An investigation of the structures of the reaction products derived from perfluorobutane-2,3-dione (PFBD) and a variety of ortho-diamines has been undertaken with the aim of determining the extent to which trifluoromethyl groups stabilize covalently bound hydrates.The substituted quinoxalines as well as the pyrido<2,3-b>pyrazine (25) and the lumazines (27), (29), and (31) were all found to exist as completely dehydrated aromatic species.Depending on the reaction conditions, both the aromatic form (33) and the stable, neutral covalent dihydrate form (34) could be obtained from the reaction of PFBD with 4,5-diamino-6-hydroxypyrimidinium sulphate (32).The pyrido<3,4-b>pyrazine system (36) as well as the pteridine (38) were also found to exist as stable, neutral covalent dihydrates in which the pyrazine ring is selectively hydrated.

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Product name:6-benzoyl-2,3-bis(trifluoromethyl)quinoxaline

Cas No:107210-65-1

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