Confirmation and prevention of halogen exchange: practical and highly efficient one-pot synthesis of dibromo- and dichloropyridazinones

被引：20

作者：

Zhang, Ji ^{[1
]}

Morton, Howard E. ^{[1
]}

Ji, Jianguo ^{[1
]}

机构：

[1] Abbott Labs, Proc Res Dept, N Chicago, IL 60064 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 49期

关键词：

pyridazinone; halogen exchange; mucohalic acid; mucochloric acid; mucobromic acid; water; one-pot process;

D O I：

10.1016/j.tetlet.2006.10.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Commercially available anilines were converted by a two step, one-pot process to the corresponding pyridazinones in good to excellent yields. During the process research, a significant halogen exchange was confirmed and prevented which allowed the process to be scaled to multikilogram quantities. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8733 / 8735

页数：3

共 18 条

[1]

Chiou George C. Y., 1999, Drugs of the Future, V24, P979, DOI 10.1358/dof.1999.024.09.858628

[2] Pyridazine derivatives.: Part 38:: Efficient Heck alkenylation at position 5 of the 6-phenyl-3(2H)-pyridazinone system [J].

Coelho, A ;

Sotelo, C ;

Novoa, H ;

Peeters, OM ;

Blaton, N ;

Raviña, E .

TETRAHEDRON LETTERS, 2004, 45 (17) :3459-3463

[3] Hybrid-designed inhibitors of p38 MAP kinase utilizing N-arylpyridazinones [J].

Colletti, SL ;

Frie, JL ;

Dixon, EC ;

Singh, SB ;

Choi, BK ;

Scapin, G ;

Fitzgerald, CE ;

Kumar, S ;

Nichols, EA ;

O'Keefe, SJ ;

O'Neill, EA ;

Porter, G ;

Samuel, K ;

Schmatz, DM ;

Schwartz, CD ;

Shoop, WL ;

Thompson, CM ;

Thompson, JE ;

Wang, RX ;

Woods, A ;

Zaller, DM ;

Doherty, JB .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (03) :349-352

[4] Isoxazolo-[3,4-d]-pyridazin-7-(6H)-one as a potential substrate for new aldose reductase inhibitors [J].

Costantino, L ;

Rastelli, G ;

Gamberini, MC ;

Giovannoni, MP ;

Dal Piaz, V ;

Vianello, P ;

Barlocco, D .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (11) :1894-1900

[5] Synthesis, activity, and molecular modeling of a new series of tricyclic pyridazinones as selective aldose reductase inhibitors [J].

Costantino, L ;

Rastelli, G ;

Vescovini, K ;

Cignarella, G ;

Vianello, P ;

DelCorso, A ;

Cappiello, M ;

Mura, U ;

Barlocco, D .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (22) :4396-4405

[6] [(3-Chlorophenyl)piperazinylpropyl]pyridazinones and analogues as potent antinociceptive agents [J].

Giovannoni, MP ;

Vergelli, C ;

Ghelardini, C ;

Galeotti, N ;

Bartolini, A ;

Dal Piaz, V .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (06) :1055-1059

[7] Synthesis and biological evaluation of novel pyridazinone-based α4 integrin receptor antagonists [J].

Gong, Yong ;

Barbay, J. Kent ;

Dyatkin, Alexey B. ;

Miskowski, Tamara A. ;

Kimball, Edward S. ;

Prouty, Stephen M. ;

Fisher, M. Carolyn ;

Santulli, Rosemary J. ;

Schneider, Craig R. ;

Wallace, Nathaniel H. ;

Ballentine, Scott A. ;

Hageman, William E. ;

Masucci, John A. ;

Maryanoff, Bruce E. ;

Damiano, Bruce P. ;

Andrade-Gordon, Patricia ;

Hlasta, Dennis J. ;

Hornby, Pamela J. ;

He, Wei .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (11) :3402-3411

[8] An efficient multikilogram synthesis of ABT-963: A selective COX-2 inhibitor [J].

Kerdesky, FAJ ;

Leanna, MR ;

Zhang, J ;

Li, WK ;

Lallaman, JE ;

Ji, JG ;

Morton, HE .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (03) :512-517

[9] New pathways towards pyridazino-fused ring systems [J].

Mátyus, P ;

Maes, BUW ;

Riedl, Z ;

Hajós, G ;

Lemière, GLF ;

Tapolcsányi, P ;

Monsieurs, K ;

Éliás, O ;

Dommisse, RA ;

Krajsovszky, G .

SYNLETT, 2004, (07) :1123-1139

[10] CARDIOTONIC AGENTS .8. SELECTIVE INHIBITORS OF ADENOSINE 3',5'-CYCLIC PHOSPHATE PHOSPHODIESTERASE-III - ELABORATION OF A 5-POINT MODEL FOR POSITIVE INOTROPIC ACTIVITY [J].

MOOS, WH ;

HUMBLET, CC ;

SIRCAR, I ;

RITHNER, C ;

WEISHAAR, RE ;

BRISTOL, JA ;

MCPHAIL, AT .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) :1963-1972

← 1 2 →