Literature DB >> 16562888

A facile access to N-sulfonylimidates and their synthetic utility for the transformation to amidines and amides.

Eun Jeong Yoo1, Imhyuck Bae, Seung Hwan Cho, Hoon Han, Sukbok Chang.   

Abstract

[reaction: see text] It is shown that N-sulfonylimidates can be efficiently prepared by a three-component coupling of terminal alkynes, sulfonyl azides, and alcohols with use of a copper catalyst and an amine base. The reaction is characterized by mild conditions, high selectivity, and tolerance with various functional groups. Facile transformation of imidates to amidines was also achieved by sodium cyanide. Additionally, a protocol for the extremely efficient Pd-catalyzed [3,3]-sigmatropic rearrangement of allylic sulfonimidates to N-allylic sulfonamides has been developed.

Entities:  

Year:  2006        PMID： 16562888     DOI： 10.1021/ol060056j

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


  10 in total

1.  An Efficient Synthesis of de novo Imidates via Aza-Claisen Rearrangements of N-Allyl Ynamides.

Authors:  Kyle A Dekorver; Troy D North; Richard P Hsung
Journal:  Synlett       Date:  2010-10       Impact factor: 2.454

Review 2.  Transition-metal-catalyzed denitrogenative transannulation: converting triazoles into other heterocyclic systems.

Authors:  Buddhadeb Chattopadhyay; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-25       Impact factor: 15.336

Review 3.  Ynamides: a modern functional group for the new millennium.

Authors:  Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

4.  N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors:  Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal:  J Org Chem       Date:  2011-05-24       Impact factor: 4.354

5.  Mass spectrometry and theoretical studies on N-C bond cleavages in the N-sulfonylamidino thymine derivatives.

Authors:  Renata Kobetić; Snježana Kazazić; Borislav Kovačević; Zoran Glasovac; Luka Krstulović; Miroslav Bajić; Biserka Žinić
Journal:  J Am Soc Mass Spectrom       Date:  2015-03-12       Impact factor: 3.109

6.  Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles.

Authors:  Tony Horneff; Stepan Chuprakov; Natalia Chernyak; Vladimir Gevorgyan; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2008-10-15       Impact factor: 15.419

7.  C-terminal peptide extension via gas-phase ion/ion reactions.

Authors:  Zhou Peng; Scott A McLuckey
Journal:  Int J Mass Spectrom       Date:  2015-08-04       Impact factor: 1.986

8.  Synthesis of amidines using N-allyl ynamides. A palladium-catalyzed allyl transfer through an ynamido-pi-allyl complex.

Authors:  Yu Zhang; Kyle A DeKorver; Andrew G Lohse; Yan-Shi Zhang; Jian Huang; Richard P Hsung
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

9.  Efficient Copper-Catalyzed Multicomponent Synthesis of N-Acyl Amidines via Acyl Nitrenes.

Authors:  Kaj M van Vliet; Lara H Polak; Maxime A Siegler; Jarl Ivar van der Vlugt; Célia Fonseca Guerra; Bas de Bruin
Journal:  J Am Chem Soc       Date:  2019-09-10       Impact factor: 15.419

10.  A facile metal-free one-pot synthesis of 3-aminoisoquinolines by intramolecular transannulation of 1-sulfonyl-4-(2-aminomethylphenyl)-1,2,3-triazoles.

Authors:  Hai Shang; Ling-Yu Li; Yu Tian; Hong-Mei Jia; Zhong-Mei Zou
Journal:  RSC Adv       Date:  2020-10-28       Impact factor: 4.036
  10 in total

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