The 1,4‐Oxazines

McKee, R. L.

doi:10.1002/9780470186787.ch15

Chemistry of Heterocyclic Compounds: A Series of Monographs

1962

DOI: 10.1002/9780470186787.ch15

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The 1,4‐Oxazines

R. L. McKee¹

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1979

1985

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Cited by 2 publications

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Studies in the heterocyclic series. XV. Synthesis and reactions of the first triazaphenoxazine ring system

Okafor

1979

Journal of Heterocyclic Chem

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1,4,9‐Benzo[b]triazaphenoxazine, the first and parent compound of this new heterocyclic ring, as well as its derivatives were prepared essentially by cyclo‐condensation of 2‐amino‐3‐hydroxypyridine with the appropriate 2,3‐dichloroquinoxaline in the presence of alkaline DMF or DMAC. Nitration of the product with mixed nitric and sulfuric acids gave the corresponding 13‐nitro derivative. Structural assignments were made by chemical evidence and by a study of the ultraviolet, infrared, nmr and mass spectra.

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Studies in the heterocyclic series. XV. Synthesis and reactions of the first triazaphenoxazine ring system

Okafor

1979

Journal of Heterocyclic Chem

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Some new aspects on the chemistry of 1,4‐benzoxazines

Chioccara¹,

Novellino

1985

Journal of Heterocyclic Chem

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3‐Methyl (3a) and 3‐t‐butyl‐1,4‐2H‐benzoxazine (3b) were synthesized by cyclization of the appropriate acetamidoketone (Scheme 1). The former is a highly unstable molecule which rapidly converts in an intractable mixture, while the latter slowly undergoes aerial oxidation affording the hemiacetal 4. The 4H‐forms of the same 3‐methyl (6a) and of the parent 1,4‐benzoxazine (9) could be obtained as 4‐acetyl derivatives. This latter, by hydrolysis, gave the cyclic trimer 10.

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The 1,4‐Oxazines

Cited by 2 publications

References 364 publications

Studies in the heterocyclic series. XV. Synthesis and reactions of the first triazaphenoxazine ring system

Studies in the heterocyclic series. XV. Synthesis and reactions of the first triazaphenoxazine ring system

Some new aspects on the chemistry of 1,4‐benzoxazines

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