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Chan‐Lam Coupling: Synthesis of N‐alkylated Derivatives of ϵ‐Caprolactams from Bicyclic Amidine DBU
Author(s) -
Surendra Babu Gogu V.,
Srinivas Keesara,
Mohan Rao Mandapati,
Sridhar Balasubramanian,
Sai Prathima Parvathaneni
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201800549
Subject(s) - chemistry , amidine , bicyclic molecule , alkylation , amination , caprolactam , nucleophile , combinatorial chemistry , organic chemistry , catalysis
The reactivity of bicyclic amidine 1,8‐diazabicyclo[5.4.0]undec‐8‐ene (DBU) with phenyl boronic acid forming N ‐ alkylated derivatives represents an advanced example to the existing classical Chan‐Lam Cross Coupling of amines. The conversion of DBU to important heterocyclic scaffolds, in which DBU is acting as a nucleophile forming N ‐ alkylated derivatives of ϵ‐caprolactam is described. This copper‐catalyzed reaction of DBU with phenylboronic acids represents a new paradigm of Chan‐Lam amination. This type of transformation has opened up a new direction for the synthesis of 1‐(3(phenyl amino) propyl)azepan‐2‐ones directly from the diimide, DBU in a single synthetic operation. The reaction was compatible with bicyclic amidines, 1,5‐diazabicyclo‐[4.3.0]non‐5‐ene (DBN) and 1,5,7 triazabicyclo[4.4.0]dec‐5‐ene (TBD), providing a robust system to access valuable bioactive ϵ‐caprolactams.