Efficient microwave-assisted synthesis of tetrahydroindazoles and their oxidation to indazoles

Synlett

Volumn , Issue 9, 2006, Pages 1369-1373

  Silva, Vera L M ^a   Silva, Artur M S ^a   Pinto, Diana C G A ^a   Cavaleiro, José A S ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

4 styrylpyrazoles; Dehydrogenation; Diels Alder cycloadditions; Indazoles; Microwave irradiation; N methylmaleimide

Indexed keywords

1 ACETYL 5 (4 ETHOXYPHENYL) 3 (2 HYDROXYPHENYL) 7 METHYL 6,8 DIOXOPYRROLO[3,4 G]5,5A,8A,8B TETRAHYDROINDAZOLE; INDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DEACETYLATION; DRUG SYNTHESIS; MICROWAVE IRRADIATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; STEREOCHEMISTRY;

EID: 33745356242     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-939715     Document Type: Article

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32. +.], 372 (25), 262 (39), 261 (67), 231 (11), 202 (10), 155 (5), 128 (6), 115 (16), 91 (29), 77 (9), 65 (9).
33. 2O: C, 78.24; H, 5.84; N, 10.14. Found:C, 77.84; H, 5.79; N, 10.02.
34. (a) Pinto, D. C. G. A.; Silva, A. M. S.; Almeida, L. M. P. M.; Carrillo, J. R.; Díaz-Ortiz, A.; de la Hoz, A.; Cavaleiro, J. A. S. Synlett 2003, 1415.
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37. 2: C, 67.36; H, 4.46; N, 8.27. Found: C, 67.48; H, 4.73; N, 8.30.
38. 2: C, 67.36; H, 4.46; N, 8.27. Found: C, 67.15; H, 4.37; N, 7.98.
39. 3-EtOAc as eluent. The residue was crystallised from EtOH to give the expected 1-acetyl-3-(2-hydroxyphenyl)-7-methyl-5-phenyl-6,8- dioxopyrrolo[3,4-g]-5,5a,8a,8b-tetrahydroindazoles (7a, 88%; 7b, 68%; 7c, 95%; 7d, 95%; 8a, 32%; 8b, 54%; 8c, 54%).
40. 3-EtOAc as eluent. The residue was recrystallised from EtOH to give 5-aryl-3-(2- hydroxyphenyl)-7-methyl-6,8-dioxopyrrolo[3,4-g]indazoles (9a from 7a, 85%; 9b from 7b, 32%; 9c from 8c, 31%; 9d from 7d, 34%).
41. +.], 326 (3), 311 (3), 284 (5), 255 (5), 226 (4), 164 (3), 91 (2).
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