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Rapid Synthesis of 2‐Alkanol‐substituted Pyrrolo[2,3‐ b ]quinoxalines from Propargylic Alcohols via Copper‐free Sonogashira Coupling Reaction at Room Temperature
Author(s) -
Fakharian Mahsa,
Keivanloo Ali,
Nabid Mohammad Reza
Publication year - 2018
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.3165
Subject(s) - chemistry , sonogashira coupling , micrococcus luteus , copper , bacillus subtilis , alkyl , coupling reaction , medicinal chemistry , combinatorial chemistry , catalysis , organic chemistry , palladium , bacteria , escherichia coli , genetics , biochemistry , biology , gene
A practical and efficient procedure is established for the synthesis of 2‐alkanol‐substituted pyrrolo[2,3‐ b ]quinoxalines by the reaction of N ‐alkyl‐3‐chloroquinoxaline‐2‐amines with propargylic alcohols. The reaction is carried out in the absence of any copper salt but in the presence of a catalytic amount of Pd(PPh 3 ) 2 Cl 2 at room temperature. The Sonogashira coupling reaction step in this procedure is fast, producing clean products with high yields without contamination by unwanted homocoupling Glaser reaction products. The synthesized pyrroloquinoxaline derivatives are also screened against the three bacterial strains Micrococcus luteus , pseudomonas aeruginosa, and Bacillus subtilis.