A Molybdenum-Catalyzed Oxidative System Forming Oxazines (Hetero-Diels−Alder Adducts) from Primary Aromatic Amines, Hydrogen Peroxide, and Conjugated Dienes

Autor:	Eval Rud Møller, Karl Anker Jørgensen
Rok vydání:	1996
Předmět:	inorganic chemicals chemistry.chemical_classification Diene Nitroso Compounds Organic Chemistry Oxazines Conjugated system Catalysis Adduct chemistry.chemical_compound chemistry Organic chemistry Hydrogen peroxide Alkyl
Zdroj:	The Journal of Organic Chemistry. 61:5770-5778
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo9608127
Popis:	The development of a new molybdenum-catalyzed procedure for the formation of oxazineshetero-Diels−Alder adductsfrom primary aromatic amines, hydrogen peroxide, and conjugated dienes is presented. The method is based on a molybdenum−peroxo complex, which in the presence of hydrogen peroxide as the terminal oxidant selectively catalyzes the oxidation of primary aromatic amines to the corresponding dienophilic nitroso compounds. The molybdenum−peroxo catalyst is under the present reaction conditions not reactive toward conjugated dienes and substituents attached to the aromatic nuclei of the primary aromatic amines. Several oxazines are synthezised following this new procedure using primary aromatic amines having either electron-withdrawing or electron-donating substituents and 1,3-cyclohexadiene as the standard diene. The scope of the new procedure is also demonstrated by the preparation of several oxazines using different alkyl- and phenyl-substituted conjugated dienes and 4-chloroaniline as precursor for ...
Databáze:	OpenAIRE
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