Chemistry of Diazafulvenium Methides in the Synthesis of Functionalized Pyrazoles | Zendy

Teresa M. V. D. Pinho e Melo | Zendy; Cláudio M. Nunes | Zendy; Maria I. L. Soares | Zendy; J.A. Paixão | Zendy; Α. Matos Beja | Zendy; Manuela Ramos Silva | Zendy

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Chemistry of Diazafulvenium Methides in the Synthesis of Functionalized Pyrazoles

Author(s) -

Teresa M. V. D. Pinho e Melo,

Cláudio M. Nunes,

Maria I. L. Soares,

J.A. Paixão,

Α. Matos Beja,

Manuela Ramos Silva

Publication year - 2007

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo070265x

Subject(s) - chemistry , sigmatropic reaction , intramolecular force , organic chemistry , sulfur

The chemistry of diazafulvenium methides generated by the thermal extrusion of sulfur dioxide from 2,2-dioxo-1H,3H-pyrazolo[1,5-c] [1,3]thiazoles is described. The diazafulvenium methides unsubstituted at C-7 participate in [8 pi + 2 pi] cycloadditions giving pyrazolo-annulated heterocycles resulting from the addition across the 1,7-position. 1-Methyl-diazafulvenium methides and 7,7-dimethyl-diazafulvenium methides undergo intramolecular sigmatropic [1,8]H shifts giving vinyl-1H-pyrazoles.

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