Literature DB >> 23265307

Direct imine acylation: rapid access to diverse heterocyclic scaffolds.

William P Unsworth1, Christiana Kitsiou, Richard J K Taylor.   

Abstract

A simple and efficient procedure to prepare a range of diverse heterocycles by the direct acylation of imines using a variety of functionalized benzoic acids is described. The methodology features a novel method for N-acyliminium ion generation followed by in situ intramolecular trapping by oxygen-, nitrogen-, sulfur- and carbon-based nucleophiles. Preliminary mechanistic studies, using ReactIR, are also reported.

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Year:  2012        PMID: 23265307     DOI: 10.1021/ol303073b

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  Intramolecular Redox-Mannich Reactions: Facile Access to the Tetrahydroprotoberberine Core.

Authors:  Longle Ma; Daniel Seidel
Journal:  Chemistry       Date:  2015-07-28       Impact factor: 5.236

2.  2-(3-Nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one.

Authors:  Hemant P Yennawar; Lee J Silverberg; Michael J Minehan; John Tierney
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-10-23

3.  6,7-Diphenyl-5-thia-7-aza-spiro-[2.6]nonan-8-one.

Authors:  Hemant P Yennawar; Lee J Silverberg
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-10-19

4.  2,3-Diphenyl-2,3,5,6-tetra-hydro-4H-1,3-thia-zin-4-one.

Authors:  Hemant P Yennawar; Lee J Silverberg
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-01-15

5.  Redox-neutral α-sulfenylation of secondary amines: ring-fused N,S-acetals.

Authors:  Claire L Jarvis; Matthew T Richers; Martin Breugst; K N Houk; Daniel Seidel
Journal:  Org Lett       Date:  2014-06-13       Impact factor: 6.005

6.  From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis.

Authors:  Sarah J Chambers; Graeme Coulthard; William P Unsworth; Peter O'Brien; Richard J K Taylor
Journal:  Chemistry       Date:  2016-03-23       Impact factor: 5.236

7.  CuI nanoparticle-catalyzed synthesis of tetracyclic benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by SNAr-type C-S, C-N bond formation from isothiocyanatobenzenes and benzimidazoles.

Authors:  Xiaolong Guo; Luyao Wang; Jing Hu; Mengmeng Zhang
Journal:  RSC Adv       Date:  2018-06-19       Impact factor: 4.036

8.  Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions.

Authors:  Thomas C Stephens; Aggie Lawer; Thomas French; William P Unsworth
Journal:  Chemistry       Date:  2018-08-19       Impact factor: 5.236

  8 in total

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