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Synthesis of Spirobicyclic Pyrazoles by Intramolecular Dipolar Cycloadditions/[1s, 5s] Sigmatropic Rearrangements.


ABSTRACT: The formation of fused pyrazoles via intramolecular 1,3-dipolar cycloadditions of diazo intermediates with pendant alkynes is described. A subsequent thermal [1s, 5s] sigmatropic shift of these pyrazole systems resulted in a ring contraction, forming spirocyclic pyrazoles. The limitations of this rearrangement were explored by changing the substituents on the nonmigrating aromatic ring and by using substrates lacking an aromatic linkage to the propargyl group.

SUBMITTER: Dimirjian CA 

PROVIDER: S-EPMC6955098 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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Synthesis of Spirobicyclic Pyrazoles by Intramolecular Dipolar Cycloadditions/[1s, 5s] Sigmatropic Rearrangements.

Dimirjian Christine A CA   Castiñeira Reis Marta M   Balmond Edward I EI   Turman Nolan C NC   Rodriguez Elys P EP   Di Maso Michael J MJ   Fettinger James C JC   Tantillo Dean J DJ   Shaw Jared T JT  

Organic letters 20190905 18


The formation of fused pyrazoles via intramolecular 1,3-dipolar cycloadditions of diazo intermediates with pendant alkynes is described. A subsequent thermal [1s, 5s] sigmatropic shift of these pyrazole systems resulted in a ring contraction, forming spirocyclic pyrazoles. The limitations of this rearrangement were explored by changing the substituents on the nonmigrating aromatic ring and by using substrates lacking an aromatic linkage to the propargyl group. ...[more]

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