Synthesis of 1- and 4-substituted piperazin-2-ones via Jocic-type reactions with N-substituted diamines

作者： Michael S. Perryman , Matthew W. M. Earl , Sam Greatorex , Guy J. Clarkson , David J. Fox

关键词: Chemistry 、 Combinatorial chemistry 、 Reduction (complexity)

摘要: Enantiomerically-enriched trichloromethyl-containing alcohols, obtained by asymmetric reduction, can be transformed regioselectively into 1-substituted piperazinones modified Jocic reactions with little or no loss of stereochemical integrity. This methodology easily used to synthesise important pharmaceutical compounds such as the fluorobenzyl intermediate a known PGGTase-I inhibitor.

参考文章(85)

Steven M Bromidge, Anthony M Brown, Stephen E Clarke, Kathy Dodgson, Tracey Gager, Helen L Grassam, Phil M Jeffrey, Graham F Joiner, Frank D King, Derek N Middlemiss, Stephen F Moss, Helen Newman, Graham Riley, Carol Routledge, Paul Wyman, None, 5-Chloro-N-(4-methoxy-3-piperazin-1-yl- phenyl)-3-methyl-2-benzothiophenesulfon- amide (SB-271046): a potent, selective, and orally bioavailable 5-HT6 receptor antagonist. Journal of Medicinal Chemistry. ,vol. 42, pp. 202- 205 ,(1999) , 10.1021/JM980532E

Heung Jae Kim, Woo Young Kwak, Jong Pil Min, Jae Young Lee, Tae Hyun Yoon, Ha Dong Kim, Chang Yell Shin, Mi Kyung Kim, Song Hyen Choi, Hae Sun Kim, Eun Kyoung Yang, Ye Hwang Cheong, Yu Na Chae, Kyung Jin Park, Ji Myun Jang, Soo Jung Choi, Moon Ho Son, Soon Hoe Kim, Moohi Yoo, Bong Jin Lee, Discovery of DA-1229: a potent, long acting dipeptidyl peptidase-4 inhibitor for the treatment of type 2 diabetes Bioorganic & Medicinal Chemistry Letters. ,vol. 21, pp. 3809- 3812 ,(2011) , 10.1016/J.BMCL.2011.04.029

Amira Y. Moreno, Alexander V. Mayorov, Kim D. Janda, Impact of distinct chemical structures for the development of a methamphetamine vaccine. Journal of the American Chemical Society. ,vol. 133, pp. 6587- 6595 ,(2011) , 10.1021/JA108807J

John T. Lai, Hindered Amines; III1. Highly Regioselective Syntheses of 1,3,3,5,5-Pentasubstituted 2-Piperazinones and their Nitroxyl Radicals Synthesis. ,vol. 1981, pp. 40- 42 ,(1981) , 10.1055/S-1981-29325

Susana Herrero, M. Teresa García-López, Miriam Latorre, Edurne Cenarruzabeitia, Joaquín Del Río, Rosario Herranz, 2-Oxopiperazine-Based γ-Turn Conformationally Constrained Peptides: Synthesis of CCK-4 Analogues Journal of Organic Chemistry. ,vol. 67, pp. 3866- 3873 ,(2002) , 10.1021/JO0256336

Christopher J. Dinsmore, Douglas C. Beshore, SYNTHESES AND TRANSFORMATIONS OF PIPERAZINONE RINGS. A REVIEW Organic Preparations and Procedures International. ,vol. 34, pp. 367- 404 ,(2002) , 10.1080/00304940209458075

Douglas C. Beshore, Christopher J. Dinsmore, Preparation of Substituted Piperazinones via Tandem Reductive Amination−(N,N‘-Acyl Transfer)−Cyclization Organic Letters. ,vol. 4, pp. 1201- 1204 ,(2002) , 10.1021/OL025644L

James E Oliver, Walter F Schmidt, Chiral 3-(hydroxymethyl)oxiranecarboxylic acids via the Jocic reaction Tetrahedron-asymmetry. ,vol. 9, pp. 1723- 1728 ,(1998) , 10.1016/S0957-4166(98)00156-6

Joanna Katarzyńska, Adam Mazur, Ewa Rudzińska, Jolanta Artym, Michał Zimecki, Stefan Jankowski, Janusz Zabrocki, Cyclolinopeptide derivatives modify methotrexate-induced suppression of the humoral immune response in mice. European Journal of Medicinal Chemistry. ,vol. 46, pp. 4608- 4617 ,(2011) , 10.1016/J.EJMECH.2011.07.040

10.

Jin-Ho Baek, Jung-In Jang, Yong-Sun Park, Asymmetric Synthesis of 3-Substituted Morpholinones and Piperazinones by L-Malate-mediated Dynamic Kinetic Resolution of α-Bromo Esters Bulletin of The Korean Chemical Society. ,vol. 32, pp. 4067- 4070 ,(2011) , 10.5012/BKCS.2011.32.11.4067

Synthesis of 1- and 4-substituted piperazin-2-ones via Jocic-type reactions with N-substituted diamines

来源期刊

我的账户

Synthesis of 1- and 4-substituted piperazin-2-ones via Jocic-type reactions with N-substituted diamines

来源期刊

相似文章 8

我的账户