Chemistry of Ketene N,S-Acetals: An Overview
- 13 January 2016
- journal article
- review article
- Published by American Chemical Society (ACS) in Chemical Reviews
- Vol. 116 (2), 287-322
- https://doi.org/10.1021/acs.chemrev.5b00360
Abstract
Push–pull alkenes, which bear electron-donating and -accepting group(s) at both termini of a C═C double bond, respectively, are of interest not only for their unique electronic properties but also for their importance as versatile building blocks in organic synthesis. In the world of ketene acetals having the push–pull alkene skeleton, ketene N,S-acetal is most likely the biggest family according to the number and types of these compounds. The first ketene N,S-acetal compound was reported in 1956. As a cyclic ketene N,S-acetal compound, nithiazine, the first lead structure of neonicotinoid insecticides, was reported in 1978. The characteristics of ketene N,S-acetals, which have the structural feature of ketene S,S-acetals and enaminones, make them versatile and easy to use, especially in cyclization and multicomponent reactions for the synthesis of various heterocyclic systems and related natural products. There has been an increasing wealth of information about the synthesis and synthetic applications of ketene N,S-acetals, especially, in recent years. This review provides comprehensive knowledge on the chemistry of ketene N,S-acetals.Keywords
Funding Information
- Program for New Century Excellent Talents in University (NCET-11-0613)
- National Natural Science Foundation of China (21272034, 21502017, 21572031)
This publication has 99 references indexed in Scilit:
- Nicotinic Acetylcholine Receptor Agonists: A Milestone for Modern Crop ProtectionAngewandte Chemie-International Edition, 2013
- Facile [7C+1C] Annulation as an Efficient Route to Tricyclic Indolizidine AlkaloidsAngewandte Chemie-International Edition, 2013
- Synthesis, crystal structure and antidiabetic activity of substituted (E)-3-(Benzo [d]thiazol-2-ylamino) phenylprop-2-en-1-oneEuropean Journal of Medicinal Chemistry, 2013
- Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moietyEuropean Journal of Medicinal Chemistry, 2010
- Copper(II) Bromide/Boron Trifluoride Etherate‐Cocatalyzed Cyclization of Ketene Dithioacetals and p‐Quinones: a Mild and General Approach to Polyfunctionalized BenzofuransAdvanced Synthesis & Catalysis, 2010
- Recent developments in the chemistry of sydnonesTetrahedron, 2010
- Domino nucleophilic trifluoromethylations of alkyl perfluorodithioestersJournal of Fluorine Chemistry, 2009
- The Liebeskind–Srogl C-C Cross‐Coupling ReactionAngewandte Chemie-International Edition, 2009
- Highly Selective Thiiranation of 1,2‐Allenyl Sulfones with Br2 and Na2S2O3: Mechanism and Asymmetric Synthesis of AlkylidenethiiranesAngewandte Chemie-International Edition, 2007
- Synthesis and herbicidal activity of 2-cyano-3-(2-fluoro-5-pyridyl)methylaminoacrylatesJournal of Fluorine Chemistry, 2005