Facile Route to Tetrasubstituted Pyrazoles Utilizing Ceric Ammonium Nitrate

被引：23

作者：

Devery, James J., III ^{[1
]}

Mohanta, Pramod K. ^{[1
]}

Casey, Brian M. ^{[1
]}

Flowers, Robert A., II ^{[1
]}

机构：

[1] Lehigh Univ, Dept Chem, Bethlehem, PA 18015 USA

来源：

SYNLETT | 2009年 / 09期

基金：

美国国家卫生研究院;

关键词：

heterocycles; pyrazoles; ceric ammonium nitrate; allylation; hydrazines; ESTROGEN-RECEPTOR-ALPHA; CLINICAL CANDIDATE; BETA; INHIBITORS; IDENTIFICATION; LIGANDS; ANTAGONISTS; DISCOVERY; OXIDATION; REAGENTS;

D O I：

10.1055/s-0029-1217163

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient approach for the synthesis of tetrasubstituted pyrazoles is described. The method involves the treatment of 1,3-diketones and allyltrimethylsilane with CAN followed by cerium-catalyzed addition of substituted hydrazines to construct pyrazoles in good yields.

引用

收藏

页码：1490 / 1494

页数：5

相关论文

共 20 条

[1] The effect of 1,3-diaryl-[1H]-pyrazole-4-acetamides on glucose utilization in ob/ob mice [J].

Bebernitz, GR ;

Argentieri, G ;

Battle, B ;

Brennan, C ;

Balkan, B ;

Burkey, BF ;

Eckhardt, M ;

Gao, JP ;

Kapa, P ;

Strohschein, RJ ;

Schuster, HF ;

Wilson, M ;

Xu, DD .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (16) :2601-2611

[2] Discovery of a novel A2B adenosine receptor antagonist as a clinical candidate for chronic inflammatory airway diseases [J].

Elzein, Elfatih ;

Kalla, Rao V. ;

Li, Xiaofen ;

Perry, Thao ;

Gimbel, Art ;

Zeng, Dewan ;

Lustig, David ;

Leung, Kwan ;

Zablocki, Jeff .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (07) :2267-2278

[3] Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens [J].

Fink, BE ;

Mortensen, DS ;

Stauffer, SR ;

Aron, ZD ;

Katzenellenbogen, JA .

CHEMISTRY & BIOLOGY, 1999, 6 (04) :205-219

[4] 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 [J].

Genin, MJ ;

Biles, C ;

Keiser, BJ ;

Poppe, SM ;

Swaney, SM ;

Tarpley, WG ;

Yagi, Y ;

Romero, DL .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) :1034-1040

[5] Mechanistic studies of Ce(IV)-mediated oxidation of β-dicarbonyls:: Solvent-dependent behavior of radical cation intermediates [J].

Jiao, Jingliang ;

Zhang, Yang ;

Devery, James J., III ;

Xu, Luna ;

Deng, Jennifer ;

Flowers, Robert A., II .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15) :5486-5492

[6] Conformational changes and coactivator recruitment by novel ligands for estrogen receptor-α and estrogen receptor-β:: Correlations with biological character and distinct differences among SRC coactivator family members [J].

Kraichely, DM ;

Sun, J ;

Katzenellenbogen, JA ;

Katzenellenbogen, BS .

ENDOCRINOLOGY, 2000, 141 (10) :3534-3545

[7]

LAURIA A, 2009, TETRAHEDRON IN PRESS

[8] Optimization of a dihydropyrrolopyrazole series of transforming growth factor-β type I receptor kinase domain inhibitors:: Discovery of an orally bioavailable transforming growth factor-β receptor type I inhibitor as antitumor agent [J].

Li, Hong-Yu ;

McMillen, William T. ;

Heap, Charles R. ;

McCann, Denis J. ;

Yan, Lei ;

Campbell, Robert M. ;

Mundla, Sreenivasa R. ;

King, Chi-Hsin R. ;

Dierks, Elizabeth A. ;

Anderson, Bryan D. ;

Britt, Karen S. ;

Huss, Karen L. ;

Voss, Matthew D. ;

Wang, Yan ;

Clawson, David K. ;

Yingling, Jonathan M. ;

Sawyer, J. Scott .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (07) :2302-2306

[9] APPLICATION OF LANTHANIDE REAGENTS IN ORGANIC-SYNTHESIS [J].

MOLANDER, GA .

CHEMICAL REVIEWS, 1992, 92 (01) :29-68

[10] Identification of novel cyclooxygenase-2 selective inhibitors using pharmacophore models [J].

Palomer, A ;

Cabré, F ;

Pascual, J ;

Campos, J ;

Trujillo, MA ;

Entrena, A ;

Gallo, MA ;

García, L ;

Mauleón, D ;

Espinosa, A .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (07) :1402-1411