Regioselective synthesis of pyrazoles fused with heteroaliphatic amines at the [3,4-c] edges

作者: Sergey P. Ivonin , Bohdan B. Kurpil’ , Dmitry M. Volochnyuk , Oleksandr O. Grygorenko

DOI: 10.1016/J.TETLET.2015.09.108

关键词:

摘要: A regioselective approach to the synthesis of 2,4,5,7-tetrahydropyrrolo[3,4-c]pyrazoles, 4,5,6,7-tetrahydropyrazolo[3,4-c]pyridines and 2,4,5,6,7,8-hexahydropyrazolo[3,4-c]azepines is described. The method relies on annulation saturated heterocyclic amine ring a suitably functionalized trisubstituted pyrazole allows for preparation target bicyclic compounds in five, six eight steps, respectively.

参考文章(20)
Daniel J. Foley, Richard G. Doveston, Ian Churcher, Adam Nelson, Stephen P. Marsden, A systematic approach to diverse, lead-like scaffolds from α,α-disubstituted amino acids Chemical Communications. ,vol. 51, pp. 11174- 11177 ,(2015) , 10.1039/C5CC03002A
Anatoliy G. Yaremenko, Dmitriy M. Volochnyuk, Vyacheslav V. Shelyakin, Oleksandr O. Grygorenko, Tetrahydropyrido[d]pyridazinones—promising scaffolds for drug discovery Tetrahedron. ,vol. 69, pp. 6799- 6803 ,(2013) , 10.1016/J.TET.2013.06.029
Alan Nadin, Channa Hattotuwagama, Ian Churcher, Lead-oriented synthesis: a new opportunity for synthetic chemistry. Angewandte Chemie. ,vol. 51, pp. 1114- 1122 ,(2012) , 10.1002/ANIE.201105840
Kentaro Futatsugi, Vincent Mascitti, Cristiano R.W. Guimarães, Nao Morishita, Cuiman Cai, Michael P. DeNinno, Hua Gao, Michael D. Hamilton, Richard Hank, Anthony R. Harris, Daniel W. Kung, Sophie Y. Lavergne, Bruce A. Lefker, Michael G. Lopaze, Kim F. McClure, Michael J. Munchhof, Cathy Preville, Ralph P. Robinson, Stephen W. Wright, Paul D. Bonin, Peter Cornelius, Yue Chen, Amit S. Kalgutkar, From partial to full agonism: Identification of a novel 2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole as a full agonist of the human GPR119 receptor Bioorganic & Medicinal Chemistry Letters. ,vol. 23, pp. 194- 197 ,(2013) , 10.1016/J.BMCL.2012.10.119
Roman Kombarov, Andrea Altieri, Dmitry Genis, Mikhail Kirpichenok, Valeriy Kochubey, Natalia Rakitina, Zoya Titarenko, BioCores: identification of a drug/natural product-based privileged structural motif for small-molecule lead discovery. Molecular Diversity. ,vol. 14, pp. 193- 200 ,(2010) , 10.1007/S11030-009-9157-5
Richard Doveston, Stephen Marsden, Adam Nelson, Towards the realisation of lead-oriented synthesis. Drug Discovery Today. ,vol. 19, pp. 813- 819 ,(2014) , 10.1016/J.DRUDIS.2013.11.006
Paul MacLellan, Adam Nelson, A conceptual framework for analysing and planning synthetic approaches to diverse lead-like scaffolds. Chemical Communications. ,vol. 49, pp. 2383- 2393 ,(2013) , 10.1039/C2CC38184B
Kazumasa Takahashi, Kenichiro Shibasaki, Katsuyuki Ogura, Hirotada Iida, Efficient method for a one-carbon homologation of aldehydes and benzophenone to carboxylic acids Journal of Organic Chemistry. ,vol. 48, pp. 3566- 3569 ,(1983) , 10.1021/JO00168A042
Michael P. Winters, Nalin Subasinghe, Mark Wall, Edward Beck, Michael R. Brandt, Michael F.A. Finley, Yi Liu, Mary Lou Lubin, Michael P. Neeper, Ning Qin, Christopher M. Flores, Zhihua Sui, Discovery and SAR of novel tetrahydropyrrolo[3,4-c]pyrazoles as inhibitors of the N-type calcium channel. Bioorganic & Medicinal Chemistry Letters. ,vol. 24, pp. 2053- 2056 ,(2014) , 10.1016/J.BMCL.2014.03.062
Thomas James, Paul MacLellan, George M. Burslem, Iain Simpson, J. Andrew Grant, Stuart Warriner, Visuvanathar Sridharan, Adam Nelson, A modular lead-oriented synthesis of diverse piperazine, 1,4-diazepane and 1,5-diazocane scaffolds Organic and Biomolecular Chemistry. ,vol. 12, pp. 2584- 2591 ,(2014) , 10.1039/C3OB42512F