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Microwave‐Assisted Synthesis of Arylated Pyrrolo[2,1‐ a ]Isoquinoline Derivatives via Sequential [3 + 2] Cycloadditions and Suzuki‐Miyaura Cross‐Couplings in Aqueous Medium
Author(s) -
Dawood Kamal M.,
Elamin Manahil B.,
Farag Ahmad M.
Publication year - 2016
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.2508
Subject(s) - isoquinoline , chemistry , bromide , aqueous medium , boronic acid , aqueous solution , aryl , solvent , organic chemistry , thiophene , combinatorial chemistry , alkyl
Treatment of 5‐bromo‐2‐(bromoacetyl)thiophene ( 1 ) with isoquinoline gave the isoquinolinium bromide 2 . Reaction of 2 with acrylic acid derivatives, in the presence of MnO 2 , afforded the 3‐[(5‐bromothiophen‐2‐ylcarbonyl]pyrrolo[2,1‐ a ]‐isoquinolines 3a , 3b . Suzuki–Miyaura cross‐coupling reactions of the bromides 3a , 3b in aqueous solvent with several activated and deactivated aryl(hetaryl)boronic acids 4a , 4b , 4c , 4d , 4e , 4f using a Pd(II)‐complex under thermal heating as well as microwave‐irradiating conditions afforded the corresponding new arylated pyrrolo[2,1‐ a ]isoquinoline derivatives 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 in high to excellent isolated yields.