Literature DB >> 28558466

Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines.

Justin M Salvant1, Anne V Edwards1, Daniel Z Kurek1, Ryan E Looper1.   

Abstract

A regioselective base-mediated cyclization of mono-N-acylpropargylguanidines is reported. A related Ag(I)-catalyzed hydroamination strategy was recently employed to yield N3-Cbz-protected ene-guanidines, which found utility in the synthesis of naamidine A. Herein, we report the base-catalyzed hydroamination of mono-N-acylpropargylguanidines, which proceeds with the opposite regiochemistry to deliver isomerized N2-acyl-2-aminoimidazoles with broad substrate scope, circumventing the problematic regiospecific acylation of free 2-aminoimidazoles.

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Year:  2017        PMID： 28558466      PMCID： PMC6016371          DOI： 10.1021/acs.joc.7b00639

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  16 in total

1.  NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities.

Authors:  Hugo E. Gottlieb; Vadim Kotlyar; Abraham Nudelman
Journal:  J Org Chem       Date:  1997-10-17       Impact factor: 4.354

2.  4,5-Di-substituted benzyl-imidazol-2-substituted amines as the structure template for the design and synthesis of reversal agents against P-gp-mediated multidrug resistance breast cancer cells.

Authors:  Nan Zhang; Zhaohui Zhang; Iris L K Wong; Shengbiao Wan; Larry M C Chow; Tao Jiang
Journal:  Eur J Med Chem       Date:  2014-06-10       Impact factor: 6.514

3.  Regioselective rhodium(II)-catalyzed hydroaminations of propargylguanidines.

Authors:  Morgan J Gainer; Nitasha R Bennett; Yu Takahashi; Ryan E Looper
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-09       Impact factor: 15.336

4.  Base-Mediated Hydroamination of Alkynes.

Authors:  Monika Patel; Rakesh K Saunthwal; Akhilesh K Verma
Journal:  Acc Chem Res       Date:  2017-01-27       Impact factor: 22.384

5.  Synthesis of Naamidine A and Selective Access to N(2)-Acyl-2-aminoimidazole Analogues.

Authors:  Joseph B Gibbons; Justin M Salvant; Rachel M Vaden; Ki-Hyeok Kwon; Bryan E Welm; Ryan E Looper
Journal:  J Org Chem       Date:  2015-09-24       Impact factor: 4.354

6.  2-Aminoimidazoles inhibitors of TGF-beta receptor 1.

Authors:  Dominique Bonafoux; Claudio Chuaqui; P Ann Boriack-Sjodin; Chris Fitch; Gretchen Hankins; Serene Josiah; Cheryl Black; Gregg Hetu; Leona Ling; Wen-Cherng Lee
Journal:  Bioorg Med Chem Lett       Date:  2008-12-11       Impact factor: 2.823

7.  Synthesis of bicyclic guanidines via cascade hydroamination/Michael additions of mono-N-acryloylpropargylguanidines.

Authors:  Ki-Hyeok Kwon; Catherine M Serrano; Michael Koch; Louis R Barrows; Ryan E Looper
Journal:  Org Lett       Date:  2014-11-13       Impact factor: 6.005

8.  A novel acylaminoimidazole derivative, WN1316, alleviates disease progression via suppression of glial inflammation in ALS mouse model.

Authors:  Kazunori Tanaka; Takuya Kanno; Yoshiko Yanagisawa; Kaori Yasutake; Satoshi Inoue; Noriaki Hirayama; Joh-E Ikeda
Journal:  PLoS One       Date:  2014-01-31       Impact factor: 3.240

9.  Synthesis of substituted 2-aminoimidazoles via Pd-catalyzed alkyne carboamination reactions. Application to the synthesis of preclathridine natural products.

Authors:  Blane P Zavesky; Nicholas R Babij; John P Wolfe
Journal:  Org Lett       Date:  2014-09-08       Impact factor: 6.005

10.  Development of a screen to identify selective small molecules active against patient-derived metastatic and chemoresistant breast cancer cells.

Authors:  Keith M Gligorich; Rachel M Vaden; Dawne N Shelton; Guoying Wang; Cindy B Matsen; Ryan E Looper; Matthew S Sigman; Bryan E Welm
Journal:  Breast Cancer Res       Date:  2013       Impact factor: 6.466
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