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Synthesis of New 1‐Hydroxyindole‐2‐Carboxylates and Mechanistic Studies on Reaction Pathways
Author(s) -
Park Yeon Kyeong,
Lee Sang Hyup
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2796
Subject(s) - chemistry , nucleophile , steric effects , condensation reaction , condensation , reaction mechanism , combinatorial chemistry , computational chemistry , stereochemistry , organic chemistry , catalysis , physics , thermodynamics
Synthesis of new 1‐hydroxyindole‐2‐carboxylates 1 and mechanistic studies on the reaction pathways were described. The substrates 2 , prepared through two‐step synthetic sequences, were treated with nucleophiles in the presence of SnCl 2 · 2H 2 O to obtain compounds 1 . In particular, the mechanistic studies led to a significant finding that reactions with thiol nucleophiles occur through a newly proposed pathway (path B: 1,4‐addition followed by reduction/condensation) rather than through a previously assumed pathway (path A: reduction/condensation followed by 1,5‐addition). Further mechanistic investigations revealed steric effects of o ‐substituents in 2 governing the ratio of products ( 1i / 7 ).