Microwave‐Assisted Synthesis of Arylated Pyrrolo[2,1‐ a ]Isoquinoline Derivatives via Sequential  [3 + 2] Cycloadditions  and  Suzuki‐Miyaura Cross‐Couplings  in Aqueous Medium | Zendy

Dawood Kamal M. | Zendy; Elamin Manahil B. | Zendy; Farag Ahmad M. | Zendy

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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.

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