Facile synthesis of 1-substituted 4,5-diaminopyrazoles and its application toward the synthesis of pyrazolo[3,4-b]pyrazines

Tetrahedron Letters

Volumn 45, Issue 21, 2004, Pages 4105-4108

  Chien, Tun Cheng ^a   Smaldone, Ronald A ^a,b   Townsend, Leroy B ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

4,5 Diaminopyrazole; Curtius rearrangement; Pyrazolo 3,4 b pyrazine

Indexed keywords

PYRAZINE DERIVATIVE; PYRAZOLE DERIVATIVE;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; CURTIUS REARRANGEMENT; HYDROGENOLYSIS; PHOTOCHEMICAL QUENCHING; POLYMERIZATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 2342626685     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.142     Document Type: Article

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19. 4. The solvent was evaporated under reduced pressure and the product was purified by recrystallization or column chromatography
20. General procedure for the preparation of 1-substituted 5-amino-4-benxyloxycarbonylaminopyrazoles 5a-c and 12: A mixture of 1-substituted 5-aminopyrazole-4-carbonylazide (3a-c or 11, 10 mmol) and benzyl alcohol (100 mmol, 10 equiv) in xylenes (125 mL) was heated at reflux temperature under an argon atmosphere. After cooling to room temperature, the solvent was evaporated under reduced pressure and the product was purified by column chromatography
21. 5: C, 44.44; H, 4.97; N, 25.91. Found: C, 44.52; H, 5.09; N, 25.74
22. 9· Na: 513.1597. Found: 513.1597
23. 4: C, 47.62; H, 4.80; N, 22.21. Found: C, 47.57; H, 4.92; N, 22.28