Literature DB >> 30354138

Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo- trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates.

Vladimir A Maslivetc1, Liliya V Frolova2, Snezna Rogelj2, Anna A Maslivetc1, Marina Rubina1, Michael Rubin1,3.   

Abstract

A strain-release-driven, cation-templated nucleophilic 7- and 8- exo-trig-cyclization of tethered Boc-protected amines to cyclopropenes is described. The featured reaction proceeds in diastereo- and regioselective fashion and allows for preparation of the corresponding 2,5-diazabicyclo[5.1.0]octan-6-ones and 2,6-diazabicyclo[6.1.0]nonan-7-ones as sole products in high yields. Preliminary studies on anticancer activities of these novel cyclopropane-fused medium heterocycles were performed.

Entities:  

Year:  2018        PMID： 30354138      PMCID： PMC6667834          DOI： 10.1021/acs.joc.8b02062

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


  34 in total

1.  Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis.

Authors:  Hans-Ulrich Reissig; Reinhold Zimmer
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

2.  A new golden age for donor-acceptor cyclopropanes.

Authors:  Tobias F Schneider; Johannes Kaschel; Daniel B Werz
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-25       Impact factor: 15.336

3.  Catalytic Enantioselective Cloke-Wilson Rearrangement.

Authors:  Alesandere Ortega; Rubén Manzano; Uxue Uria; Luisa Carrillo; Efraim Reyes; Tomas Tejero; Pedro Merino; Jose L Vicario
Journal:  Angew Chem Int Ed Engl       Date:  2018-06-04       Impact factor: 15.336

4.  Directed Cu(I)-Catalyzed Carbomagnesiation of 1-Arylcycloprop-2-ene-1-carboxamides En Route to Densely Substituted Functionalized Cyclopropanes.

Authors:  Andrew Edwards; Michael Rubin
Journal:  J Org Chem       Date:  2018-07-06       Impact factor: 4.354

5.  Asymmetric Copper-Catalyzed Carbozincation of Cyclopropenes en Route to the Formation of Diastereo- and Enantiomerically Enriched Polysubstituted Cyclopropanes.

Authors:  Daniel S Müller; Ilan Marek
Journal:  J Am Chem Soc       Date:  2015-12-01       Impact factor: 15.419

6.  Recent developments of cyclopropene chemistry.

Authors:  Zhi-Bin Zhu; Yin Wei; Min Shi
Journal:  Chem Soc Rev       Date:  2011-06-22       Impact factor: 54.564

7.  Diastereoselectivity control in formal nucleophilic substitution of bromocyclopropanes with oxygen- and sulfur-based nucleophiles.

Authors:  Joseph E Banning; Anthony R Prosser; Bassam K Alnasleh; Jason Smarker; Marina Rubina; Michael Rubin
Journal:  J Org Chem       Date:  2011-04-14       Impact factor: 4.354

8.  Synthesis of Novel c(AmpRGD)-Sunitinib Dual Conjugates as Molecular Tools Targeting the αvβ3 Integrin/VEGFR2 Couple and Impairing Tumor-Associated Angiogenesis.

Authors:  Andrea Sartori; Elisabetta Portioli; Lucia Battistini; Lido Calorini; Alberto Pupi; Federica Vacondio; Daniela Arosio; Francesca Bianchini; Franca Zanardi
Journal:  J Med Chem       Date:  2016-12-20       Impact factor: 7.446

9.  Highly enantioselective synthesis of 2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-ones via catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization.

Authors:  Yuwei He; Chuyu Cheng; Bin Chen; Kun Duan; Yue Zhuang; Bo Yuan; Meisan Zhang; Yougui Zhou; Zihong Zhou; Yu-Jun Su; Rihui Cao; Liqin Qiu
Journal:  Org Lett       Date:  2014-12-03       Impact factor: 6.005

10.  Desymmetrization of Cyclopropenes via the Potassium-Templated Diastereoselective 7- exo- trig Cycloaddition of Tethered Amino Alcohols toward Enantiopure Cyclopropane-Fused Oxazepanones with Antimycobacterial Activity.

Authors:  Vladimir A Maslivetc; Danielle N Turner; Kimberly N McNair; Liliya Frolova; Snezna Rogelj; Anna A Maslivetc; Nicolai A Aksenov; Marina Rubina; Michael Rubin
Journal:  J Org Chem       Date:  2018-05-02       Impact factor: 4.354
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  1 in total

1.  Facile assembly of 1,5-diazocan-2-ones via cyclization of tethered sulfonamides to cyclopropenes.

Authors:  Jonathon P Matheny; Pavel M Yamanushkin; Peter A Petillo; Michael Rubin
Journal:  RSC Adv       Date:  2020-12-15       Impact factor: 4.036
  1 in total

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