Literature DB >> 35084425

An amine template strategy to construct successive C-C bonds: synthesis of benzo[h]quinolines by a deaminative ring contraction cascade.

Timothy Patrick McFadden1, Chideraa Iheanyi Nwachukwu1, Andrew George Roberts1.   

Abstract

We developed a convergent strategy to build, cyclize and excise nitrogen from tertiary amines for the synthesis of polyheterocyclic aromatics. Biaryl-linked azepine intermediates can undergo a deaminative ring contraction cascade reaction, excising nitrogen with the formation of an aromatic core. This strategy and deaminative ring contraction reaction are useful for the synthesis of benzo[h]quinolines.

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Year:  2022        PMID: 35084425      PMCID: PMC8957836          DOI: 10.1039/d1ob02245h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  41 in total

1.  Ambient Temperature, Ullmann-like Reductive Coupling of Aryl, Heteroaryl, and Alkenyl Halides.

Authors:  Shijie Zhang; Dawei Zhang; Lanny S. Liebeskind
Journal:  J Org Chem       Date:  1997-04-18       Impact factor: 4.354

2.  Total synthesis of the Cephalotaxus alkaloids. A problem in nucleophilic aromatic substitution.

Authors:  M F Semmelhack; B P Chong; R D Stauffer; T D Rogerson; A Chong; L D Jones
Journal:  J Am Chem Soc       Date:  1975-04-30       Impact factor: 15.419

3.  Synthesis of santiagonamine.

Authors:  Michael D Markey; Ying Fu; T Ross Kelly
Journal:  Org Lett       Date:  2007-07-21       Impact factor: 6.005

Review 4.  The art of total synthesis through cascade reactions.

Authors:  K C Nicolaou; Jason S Chen
Journal:  Chem Soc Rev       Date:  2009-04-21       Impact factor: 54.564

5.  Directed heterodimerization: stereocontrolled assembly via solvent-caged unsymmetrical diazene fragmentation.

Authors:  Mohammad Movassaghi; Omar K Ahmad; Stephen P Lathrop
Journal:  J Am Chem Soc       Date:  2011-08-01       Impact factor: 15.419

Review 6.  Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Authors:  Amanda C Jones; Jeremy A May; Richmond Sarpong; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-03       Impact factor: 15.336

Review 7.  Stereoselective total synthesis of axially chiral natural products via biaryl lactones.

Authors:  G Bringmann; D Menche
Journal:  Acc Chem Res       Date:  2001-08       Impact factor: 22.384

8.  Synthesis of substituted 8-aminoquinolines and phenanthrolines through a Povarov approach.

Authors:  Kavita De; Julien Legros; Benoit Crousse; Srinivasan Chandrasekaran; Danièle Bonnet-Delpon
Journal:  Org Biomol Chem       Date:  2010-10-18       Impact factor: 3.876

9.  Substituted 2,2'-bipyridines by nickel-catalysis: 4,4'-di-tert-butyl-2,2'-bipyridine.

Authors:  Joseph A Buonomo; Daniel A Everson; Daniel J Weix
Journal:  Synthesis (Stuttg)       Date:  2013-11-01       Impact factor: 3.157

10.  Intramolecular asymmetric reductive amination: synthesis of enantioenriched dibenz[c,e]azepines.

Authors:  Tao Yang; Xiaochong Guo; Qin Yin; Xumu Zhang
Journal:  Chem Sci       Date:  2018-12-27       Impact factor: 9.825

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