Unexpected ring closure between hydrazono and nitro groups: A useful synthesis of substituted pyrazole N-oxides

Synlett

Volumn , Issue 17, 2006, Pages 2731-2734

  Attanasi, Orazio A ^a   Favi, Gianfranco ^a   Filippone, Paolino ^a   Giorgi, Gianluca ^b   Lillini, Samuele ^a   Mantellini, Fabio ^a   Perrulli, Francesca R ^a  

^a UNIVERSITY OF URBINO   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

1,2 diaza 1,3 butadienes; Hydrazones; Michael additions; Nitro compounds; Pyrazole N oxides

Indexed keywords

1,2 DIAZA 1,3 BUTADIENE; 1,3 BUTADIENE DERIVATIVE; BETA NITROHYDRAZONE; HYDRAZONE DERIVATIVE; NITROALKANE; PYRAZOLE DERIVATIVE; PYRAZOLE N OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; RING CLOSING METATHESIS; SYNTHESIS;

EID: 33750511309     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950258     Document Type: Article

References (34)

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22. 5: C, 50.90; H, 7.93; N, 16.96. Found: C, 51.00; H, 7.91; N, 16.95.
23. Synthesis of Pyrazole-1-oxides 4a-n; General Procedure: A solution of β-nitrohydrazone 3a-n (2 mmol) and NaOMe (108 mg, 2 mmol) in MeOH (20 mL) was refluxed until complete disappearance of 3a-n was observed (monitored by silica gel TLC, for time see Table 2). The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel (elution mixture: EtOAc-MeOH = 95:5). Finally, products 4a-n were crystallized from hot EtOAc-MeOH.
24. 4: C, 53.83; H, 7.74; N, 17.94. Found: C, 53.87; H, 7.76; N, 17.91.
25. 4: C, 56.45; H, 8.29; N, 16.46. Found: C, 56.31; H, 8.31; N, 16.51.
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34. Crystallographic data (excluding structure factors) for compound 4d have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 621653 ([a] Polymorph 1) and CCDC 621654 ([b] Polymorph 2). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].