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Photorearrangement of spiro-oxaziridines - applications in the syntheses of hexahydro-5H-pyrrolo-[2]benzazepin-5-ones and a tetrahydro-1H,5H-pyrroloisoquinolin-5-one

✍ Scribed by G.P. Johnson; B.A. Marples

Book ID
104222498
Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
206 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

We have recently established' that Spiro-oxaziridines (1), in which the N-alkyl group is anti to the aromatic ring, photorearrange regiospecifically to the benzazepinones (2). The migration of the saturated ring carbon atom, which is anti to the nitrogen lone pair, is in accordance with observations made in the photolysis of related non-aromatic compounds.2 We anticipated that Spiro-oxaziridines of the type (3) should therefore regiospecifically photorearrange to the tricyclic lactams (4). Additionally,the regioisomers(5) would be expected to give the isomeric lactams (6). We report here the synthesis of pyrrolobenzazepinones (4, R=Me, n=2) and (6, R=Me, n=2) and the pyrroloisoquinolone (4, R=Me, n=l) using this strategy.

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## Abstract Fused tricyclic 7‐phenyl‐5__H__‐thizolo[5,4‐__e__]pyrrolo[1,2‐__a__][1,4]diazepin‐10(9__H__)one (**10**) was prepared by thermolysis of 2‐phenyl‐4‐(1‐pyrrolylmethyl)thiazole‐5‐carbonyl azide (**9**) in acetic acid. In addition, starting from **10**, 7‐phenyl‐5__H__‐thiazolo [5,4‐__e__][