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Expedited Route to Fully Substituted Amino-Pyrazole Building Blocks and Their Further Transformations.


ABSTRACT: We report here an efficient and easily reproducible two-step approach to heterocycle-substituted amino-pyrazoles from heterocyclic acetonitriles and their unprecedented subsequent transformations to fully substituted pyrazoles. Such transformations include regioselective derivatization from polyamino derivatives, formation of tetracyclic compounds in up to 45% overall yield, and deaminative transformations through diazotization, followed by arylation through Suzuki-Miyaura cross-coupling and C-H activation, providing arylated pyrazoles in up to 71% yield over four steps. This strategy allows the swift introduction of significant molecular complexity to a range of scaffolds.

SUBMITTER: Kuleshova O 

PROVIDER: S-EPMC6645537 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Expedited Route to Fully Substituted Amino-Pyrazole Building Blocks and Their Further Transformations.

Kuleshova Olena O   Khilya Olga O   Volovenko Yulian Y   Mallet-Ladeira Sonia S   Dyakonenko Viktoriya V   Gras Emmanuel E  

ACS omega 20171213 12


We report here an efficient and easily reproducible two-step approach to heterocycle-substituted amino-pyrazoles from heterocyclic acetonitriles and their unprecedented subsequent transformations to fully substituted pyrazoles. Such transformations include regioselective derivatization from polyamino derivatives, formation of tetracyclic compounds in up to 45% overall yield, and deaminative transformations through diazotization, followed by arylation through Suzuki-Miyaura cross-coupling and C-H  ...[more]

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