Premium
Synthesis of 4‐Substituted Pyrrolo[2, 3‐ c ]quinolines via Microwave‐Assisted C‐N Bond Formation
Author(s) -
Penjarla Thirupathi Reddy,
Kundarapu Maheshwar,
Baquer Syed Mohd.,
Bhattacharya Anupam
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800614
Subject(s) - quinoline , chemistry , bromine , combinatorial chemistry , molecule , microwave , selectivity , medicinal chemistry , organic chemistry , catalysis , computer science , telecommunications
A metal‐free approach for the synthesis of 4‐substituted pyrolo[2, 3‐ c ]quinoline is reported in this paper. Synthesis of the target molecule started from easily available quinoline and was carried out in five steps. The fused pyrrolo‐quinoline unit was assembled using Bartoli indolization and the crucial final step involving microwave assisted C−N bond formation was carried out by reaction of 4‐chloro‐3 H ‐pyrrolo[2, 3‐ c ]quinolines and diverse aliphatic amines, in the presence of N , N ’‐diisopropylethylamine (DIPEA). Final molecules were obtained in good yields even in the presence of additional bromine functionality on the quinolines, thus demonstrating the selectivity of the developed coupling procedure and possibility of increasing the product diversity.