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Stereoselective Construction of Spiro‐Indolenine Frameworks through a Prins/Friedel–Crafts Cyclization Cascade Reaction
Author(s) -
Chandrashekhar Rapelli,
Vemulapalli Sahithya Phani Babu,
Sridhar Balasubramanian,
Subba Reddy Basireddy Venkata
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701812
Subject(s) - chemistry , friedel–crafts reaction , prins reaction , trifluoroacetic acid , stereoselectivity , trifluoroacetic anhydride , derivative (finance) , organic chemistry , cascade , catalysis , chromatography , financial economics , economics
A strategy has been developed for the synthesis of dispiro‐3 H ‐indoles by employing a 3‐({[2‐(1 H ‐indol‐3‐yl)ethyl]amino}methyl)but‐3‐en‐1‐ol derivative and various aldehydes in a sequential Prins/Friedel–Crafts cyclization in the presence of readily accessible trifluoroacetic acid (TFA) under mild conditions over a short period of time. This method proceeded smoothly with a wide range of aldehydes and provided the products in good yields with a broad pattern of substituents.