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Rh(II)‐Catalyzed Denitrogenative Reaction of 1,2,3‐Triazolyl Esters with Indoles or Arenes: Efficient Synthesis of Homotryptamines or Allylamines
Author(s) -
Pal Kuntal,
Sontakke Geetanjali S.,
Volla Chandra M. R.
Publication year - 2020
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.202000632
Subject(s) - chemistry , regioselectivity , catalysis , intramolecular force , combinatorial chemistry , nucleophile , substrate (aquarium) , tandem , cascade reaction , surface modification , nucleophilic addition , organic chemistry , oceanography , materials science , composite material , geology
An efficient strategy for the synthesis of structurally diverse homotryptamines and allyl amines via a Rh(II)‐catalyzed tandem reaction of 1,2,3‐triazolyl esters with either indoles or 1,3,5‐trimethoxybenzene has been developed. The reaction proceeds via Rh(II)‐catalyzed intramolecular rearrangement of triazoles into 1‐azadienes followed by regioselective nucleophilic addition. The efficiency of the current protocol was illustrated by broad substrate scope, gram scale synthesis and further functionalization of homotryptamines into other biologically relevant heterocycles.