Ring transformations of heterocyclic compounds. XX Benzo-fused spiro[cyclohexadiene-dihydroindoles] by ring transformation of pyrylium salts with anhydrobases of benzo[e]- and benzo[g]indolium salts
✍ Scribed by Thomas Zimmermann
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2000
- Tongue
- English
- Weight
- 366 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
The diastereoselective synthesis of 6‐aroyl‐3,5‐diarylspiro[cyclohexa‐2,4‐diene‐1,2′2′,3′‐dihydro‐1′H‐benzo[e]indoles] 6 and ‐benzo[g]indoles] 7 from 2,4,6‐triarylpyrylium perchlorates 1 and in situ generated 2‐methylene‐2,3‐dihydro‐1__H__‐benzo[e]indoles 3 or ‐benzo[g]indoles 5 (anhydrobases of the corresponding 2‐methyl‐1__H__‐benzo[e]indolium perchlorates 2 and 2‐methyl‐3__H__‐benzo[g]indolium perchlorates 4, respectively) in the presence of triethylamine/acetic acid in ethanol by a 2,5‐[C~4~+C~2~] pyrylium ring transformation is reported. Spectroscopic data of the transformation products and their mode of formation are discussed.
📜 SIMILAR VOLUMES
## Abstract 2,4,6‐Triarylpyrylium salts 1 react with the __in situ__ generated anhydrobase of 9,10‐dimethylacridinium methosulfate (2a) in the presence of anhydrous sodium acetate in ethanol by a 2,5‐[C~4~+C~2~] pyrylium ring transformation to give the hitherto unknown 6‐aroyl‐3,5‐diaryl‐10′‐methyl
## Abstract The diastereoselective synthesis of 6‐aroyl‐3,5‐diarylspiro[cyclohexa‐2,4‐diene‐1,2′‐indolines] 4 possessing three stereocenters from 2,4,6‐triarylpyrylium perchlorates 1 and chiral methyleneindolines 3 (generated __in situ__ by deprotonation of the corresponding 3__H__‐indolium perchlo