One-pot facile conversion of Baylis-Hillman adducts into 1,5-diarylpyrazoles using microwave irradiation

被引：26

作者：

Mamaghani, M. ^{[1
]}

Tabatabaeian, K. ^{[1
]}

Mirzaeinejad, M. ^{[1
]}

Nikpassand, M. ^{[1
]}

机构：

[1] Univ Guilan, Fac Sci, Dept Chem, Rasht, Iran

来源：

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY | 2006年 / 3卷 / 01期

关键词：

Baylis-Hillman; 1,5-diarylpyrazole; microwave;

D O I：

10.1007/BF03245796

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Several Baylis-Hillman adducts were prepared by the reaction of appropriate arylaldehydes with methyl vinyl ketone in the presence of imidazole and a catalytic amount of L-proline, in 55-90% yields. An easy transformation of these adducts into 1,5-diarylpyrazoles was achieved using microwave irradiation ( 400 W) with short reaction times (1-3 min) and high yields (80-91%).

引用

页码：89 / 92

页数：4

共 12 条

[1] A general, [1+4] approach to the synthesis of 3(5)-substituted pyrazoles from aldehydes.
Almirante, N
Cerri, A
Fedrizzi, G
Marazzi, G
Santagostino, M
[J]. TETRAHEDRON LETTERS, 1998, 39 (20) : 3287 - 3290
[2] Cacchi S, 1997, SYNLETT, P959
[3] Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: Lead identification and SAR of 3-and 4-substituted derivatives
Genin, MJ
Biles, C
Keiser, BJ
Poppe, SM
Swaney, SM
Tarpley, WG
Yagi, Y
Romero, DL
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) : 1034 - 1040
[4] Application of the palladium-catalyzed N-arylation of hydrazones to deactivated heteroaryl halides in the synthesis of pyrazoles
Haddad, N
Salvagno, A
Busacca, C
[J]. TETRAHEDRON LETTERS, 2004, 45 (30) : 5935 - 5937
[5] Regioselective synthesis of 1,3,5-triaryl-4-alkylpyrazoles: Novel ligands for the estrogen receptor
Huang, YR
Katzenellenbogen, JA
[J]. ORGANIC LETTERS, 2000, 2 (18) : 2833 - 2836
[6] Fused pyrazolo heterocycles: Intramolecular [3+2]-nitrile oxide cycloadditions applied to syntheses of pyrazolo[3,4-g][2,1]dihydrobenzoisoxazol(in)es
Kizer, DE
Miller, RB
Kurth, MJ
[J]. TETRAHEDRON LETTERS, 1999, 40 (18) : 3535 - 3538
[7] Regioselective synthesis of 1,3,4,5-tetrasubstituted pyrazoles from Baylis-Hillman adducts
Lee, KY
Kim, JM
Kim, JN
[J]. TETRAHEDRON LETTERS, 2003, 44 (35) : 6737 - 6740
[8] SYNTHESIS, MECHANISM OF ACTION, AND QSAR OF HERBICIDAL 3-SUBSTITUTED-2-ARYL-4,5,6,7-TETRAHYDROINDAZOLES
LYGA, JW
PATERA, RM
PLUMMER, MJ
HALLING, BP
YUHAS, DA
[J]. PESTICIDE SCIENCE, 1994, 42 (01): : 29 - 36
[9] An easy conversion of the Baylis-Hillman adducts into tert-butyldimethylsilyl ethers with tert-butyldimethylsilyl chloride and Li2S
Mamaghani, M
Badrian, A
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (12) : 2429 - 2435
[10] A facile conversion of the Baylis-Hillman adducts into trimethylsilyl ethers with hexamethyldisilazane catalysed by iodine
Mamaghani, M
Badrian, A
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2004, 179 (06) : 1181 - 1186

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