Ring transformation of spirocyclopropanepyrazoles into pyrano[2,3‐ c ]pyrazoles | Zendy

Maruoka Hiroshi | Zendy; Masumoto Eiichi | Zendy; Eishima Takafumi | Zendy; Okabe Fumi | Zendy; Nishida Sho | Zendy; Yoshimura Yuki | Zendy; Fujioka Toshihiro | Zendy; Yamagata Kenji | Zendy

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Ring transformation of spirocyclopropanepyrazoles into pyrano[2,3‐ c ]pyrazoles

Author(s) -

Maruoka Hiroshi,

Masumoto Eiichi,

Eishima Takafumi,

Okabe Fumi,

Nishida Sho,

Yoshimura Yuki,

Fujioka Toshihiro,

Yamagata Kenji

Publication year - 2009

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.117

Subject(s) - chemistry , sodium hydride , intramolecular force , ring (chemistry) , hydride , medicinal chemistry , michael reaction , pyrazole , transformation (genetics) , stereochemistry , organic chemistry , catalysis , hydrogen , biochemistry , gene

An approach to pyrano[2,3‐ c ]pyrazoles starting from spirocyclopropanepyrazoles via a ring‐opening/cyanomethylation and intramolecular cyclization is described. Reactions of spirocyclopropanepyrazoles 1a , 1b , 1c , 1d with chloroacetonitrile in the presence of sodium hydride gave the corresponding cyanomethoxypyrazoles 4a , 4b , 4c , 4d . Treatment of 4a , 4b , 4c , 4d with sodium hydride at room temperature caused intramolecular Michael addition reaction to afford the corresponding pyrano[2,3‐ c ]pyrazoles 5a , 5b , 5c , 5d . J. Heterocyclic Chem., (2009).

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