Tetrahedron p. 9667 - 9676 (1998)
Update date:2022-09-26
Topics:
Despinoy, Christophe
Lloyd, Douglas
McNab, Hamish
Reed, David
Gas-phase pyrolysis of the 2,4-diphenyl- and 2,4-dimethyl-1,5- benzodiazepines 3 and 4 at 800-850 °C gave a range of heterocyclic products (e.g. quinoxalines 8, 10 and 11, indole 9, benzimidazole 5 and pyrazole 7) in low yields. The formation of most products is initiated by cleavage of the 2,3-bond to give a diradical intermediate, though the pyrazole is obtained by a mechanism involving a 1,5-hydrogen shift followed by an unusual ring contraction.
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