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C–H Arylation of N ‐Heteroarenes under Metal‐Free Conditions and its Application towards the Synthesis of Pentabromo‐ and Pentachloropseudilins
Author(s) -
Kumar Mukesh,
Sharma Shweta,
Sil Parijat,
Kushwaha Manoj,
Mayor Satyajit,
Vishwakarma Ram A.,
Singh Parvinder Pal
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900353
Subject(s) - chemistry , aniline , reagent , combinatorial chemistry , hydrochloride , aryl , salt (chemistry) , metal , organic chemistry , alkyl
Herein, we are reporting metal‐free conditions for radical initiation and direct C–H arylation of N ‐heteroarenes. Starting from aniline, the corresponding arenediazonium salt generated in situ is reduced to an aryl radical in the presence of chloropromazine hydrochloride, a new reagent for this application. The optimized procedures are mild, operationally simple, and are working successfully with more diverse substrates in comparison to reported methods. The optimized method is also employed for the synthesis of marine natural products Pentabromo‐ and Pentachloropseudilins (PBP/PCP) . In the present study, we also validated the potential of the Pentachloropseudilin (PCP), thus synthesized, for inhibition of Myosin1 function in mammalian cells and confirmed that PCP phenocopies Myosin1c depletion in cells.