First synthesis of a bromonitrilimine. Direct formation of 3- bromopyrazole derivatives

Tetrahedron Letters

Volumn 40, Issue 13, 1999, Pages 2605-2606

  Foti, Francesco ^a   Grassi, Giovanni ^a   Risitano, Francesco ^a  

^a UNIVERSITY OF MESSINA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BROMONITRILAMINE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; NONHUMAN; REACTION ANALYSIS; SYNTHESIS;

EID: 0033605872     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00227-0     Document Type: Article

References (17)

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11. A typical procedure for the cycloaddition: To a stirred solution of phenylhydrazone 1 (10 mmol) in DMF (20 ml) at -5°C was added dropwise a solution of NBS (20 mmol) in DMF (20 ml) under an atmosphere of nitrogen. After additional stirring (15 min) at room temperature, dipolarophile a (50 mmol) was added and then dropwise TEA (10 mmol). The reaction mixture was left to stand for 2 hours, poured into cold water (100 ml) and extracted three times with ether; the organic layer was washed with water and brine, dried over anhydrous sodium sulphate and concentrated. The cycloadduct 4a was isolated by flash chromatography on silica gel (eluent: ethyl ether/petroleum ether=1/4).
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