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Selective 5‐ exo‐dig Cyclization of in Situ Synthesized N ‐Boc‐2‐aminophenyl Ethoxyethynyl Carbenols: Synthesis of Multifunctional Indoles and Their Derivatives
Author(s) -
Thirupathi Nuligonda,
Kumar Yalla Kiran,
Kant Ruchir,
Reddy Maddi Sridhar
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201301002
Subject(s) - chemistry , dig , isomerization , adduct , carbazole , nucleophile , indole test , alcohol , functional group , stereochemistry , aryl , combinatorial chemistry , in situ , medicinal chemistry , organic chemistry , catalysis , polymer , alkyl , computer security , computer science
A method to prepare 3‐substituted‐2‐formylindole derivatives from N ‐Boc‐ ortho ‐aminoaryl ketones and ethoxyacetylene through a cascade of reactions in a single operation that included a nucleophile‐triggered 5‐ exo‐dig cyclization and an acid‐mediated 1,3‐allyl alcohol isomerization (1,3‐AAI) is described. A variety of aryl, vinyl and alkynyl groups can be introduced at C‐3 of indole‐2‐carboxaldehyde while having a high functional group compatibility. The 3‐alkynyl adducts, which are highly valuable substrates for diversity‐oriented synthesis, can be further transformed to useful carboline and carbazole derivatives through novel pathways.