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Synthese 2-substituierter 1H-Benz[e][1,4]oxazepin-5-one

✍ Scribed by Dr. Dieter Sicker

Book ID: 105353685
Publisher: John Wiley and Sons
Year: 1990
Tongue: English
Weight: 467 KB
Volume: 332
Category: Article
ISSN: 1615-4150
DOI: 10.1002/prac.19903320310

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✦ Synopsis

Synthesis of 2‐Substituted 1 H‐Benz[e][1,4]oxazepin‐5‐ones

An approach to the hitherto unknown class of 1H‐benz[e][1,4]oxazepin‐5‐ones is given based on reduction and cyclization of appropriate acyclic ortho‐nitro compounds as starting materials. Thus, some 2‐substituted derivatives (3a–i) were synthesized by catalytic hydrogenation of acyl 2‐nitrobenzoates (1a–i) to yield the corresponding anthranilic acid esters (2a–i), which were subsequently cyclized in polyphosphoric acid at elevated temperature. The behaviour of esters 1a–i towards spontaneous intramolecular reductive cyclization is discussed in comparison to that of similar educts leading to sixmembered heterocycles as shown by former results.

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