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Synthesis of 1,2,3,3a,8,8a-hexahydroindeno[2,1-b]pyrrole

✍ Scribed by P.S. Anderson; G.F. Lundell; J.L. Cias; F.M. Robinson


Book ID
104247907
Publisher
Elsevier Science
Year
1971
Tongue
French
Weight
195 KB
Volume
12
Category
Article
ISSN
0040-4039

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✦ Synopsis


Although a synthesis of 1,3a,8,8a-tetrahydroindeno[2,1-blpyrrole (I) has been described,' a convenient approach to 1,2,3,3a,8,8a-hexshydroindeno[2,1-blpyrrole (II) has not been reported? It is the purpose of this communication to outline a general synthetic route to this new class of heterocyclic compounds. The route to II described here involves the construction of a pyrrolidine ring on an indane backbone as indicated in the following scheme. The pyrrolidine ensmine II of 2-indanone3 has been reported by Blomquist and Moriconi.' The enamine III was alkylated with ethyl bromoacetate in acetonitrile to provide a 63% yield after hydrolysis of ethyl indan-2-one-l-ylacetate (IV), b.p. 11Y-121Β°C at 0.05 nrm; m.p. 47-48'C. The structure of IV was elucidated by the following physical data. IV:~~~m 1750, 1725, 750 cm-l; m/e 218 @); jyp (CDCl,) 1.15 (3H, t, J=7.5 Hz), 2.95 (a, d, J=5.5 Rs), 3.55 (21I, s), 3.70 (Ui, t, J=5.5 Hz), 4.05 (al, q, J=7.5 Hs), 7.25 (4% s). Treatment of the ketone IV with hydroxylamine hydrochloride in moist ether containing sodium bicarbonate provided an 85$ yield of a mixture of the syn and anti-oximes V, m.p. 77-880c;flmZl 3200, 1725, 1675. 1175, 750 cm-'. The mixture of oximes V was subjected to reductive cyclisation over 5s PI/C in acetic acid containing 105 by weight sulfuric acid to provide in 73% yield the lactem VI, m.p. 1.89'~. The structure was confirmed by the following physical data.


πŸ“œ SIMILAR VOLUMES


A stereoselective synthesis of 3-substit
✍ John D. Harling; Barry S. Orlek πŸ“‚ Article πŸ“… 1998 πŸ› Elsevier Science 🌐 French βš– 422 KB

3-Substituted hexahydroindeno[2,1-b]pyrroles were prepared in a stereoselective manner in high yield v/a an intramolecular azomethine ylide cycloaddition. Olefin geometry in the ylide precursor controlled the stereochemistry at the 3position.