Montmorillonite K-10 Clay Promoted Direct Dehydrative Nucleophilic Substitution of Pyrrole and Indole with 4-Chromanols

A mild and inexpensive method of alkylation of pyrrole and indole with substituted 4chromanols and 3-arylidene-4-chromanols mediated by montmorillonite K-10 is reported. Indole and pyrrole upon treatment with 4-chromanols in the presence of activated montmorillonite K-10 undergo facile nucleophilic...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 13; no. 1
Main Authors Begum, Ayisha F., Balasubramanian, Kalpattu K., Shanmugasundaram, Bhagavathy
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.01.2024
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
MILD
Heterogeneous catalysis
ACID
Chromanols
Montmorillonite K-10
Direct dehydrative nucleophilic substitution
DERIVATIVES
3-arylidene-4-chromanols
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Summary:A mild and inexpensive method of alkylation of pyrrole and indole with substituted 4chromanols and 3-arylidene-4-chromanols mediated by montmorillonite K-10 is reported. Indole and pyrrole upon treatment with 4-chromanols in the presence of activated montmorillonite K-10 undergo facile nucleophilic substitution under ambient condition to afford 2-(chroman-4-yl)-1H-pyrrole and 3-(chroman-4-yl)-1H-indole in moderate to good yields. In the case of 3-arylidene-4-chromanols, this direct dehydrative substitution reaction is found to be highly regioselective affording only the respective C-4 substituted (arylidene-chroman-4-yl)- pyrrole/indole derivatives. A simple, efficient & facile protocol have been developed towards the synthesis of novel chroman-4-yl-pyrrole and chroman-4-yl-indole via direct dehydrative nucleophilic substitution of 4-chromanols with pyrrole and indole mediated by montmorillonite K-10 clay.image
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202300498