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One pot synthesis of substituted dihydroindeno[1,2-b]indoles and dihydrobenzo[a]carbazoles by photostimulated reactions of o-iodoaniline with carbanions by the SRN1 mechanism

✍ Scribed by Silvia M. Barolo; Roberto A. Rossi; Ceciréa Rosales; Jorge E. Angel Guío


Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
309 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

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The photostimulated reaction of enolate anions of cyclic aromatic ketones such as substituted indan‐1‐ones and 3,4‐dihydro‐2__H__‐naphthalen‐1‐one with o‐iodoaniline in DMSO affords 1‐, 2‐, 3‐, and 4‐methoxy‐5,10‐dihydroindeno[1,2‐b]indoles (34‐40%), 1,2‐, 1,4‐, and 2,3‐dimethoxy‐5,10‐dihydroindeno[1,2‐b]‐indoles (31‐43%), and 1‐, 2‐, and 3‐methoxy‐5,11‐dihydro‐6__H__‐benzo[a]carbazoles (42‐61%) by the S~RN~1 mechanism in one pot reactions.


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