Vilsmeier reaction of enaminones: efficient synthesis of halogenated pyridin-2(1H)-ones
- PMID: 19006368
- DOI: 10.1021/jo801959j
Vilsmeier reaction of enaminones: efficient synthesis of halogenated pyridin-2(1H)-ones
Abstract
A facile and efficient one-pot synthesis of halogenated pyridin-2(1H)-ones from a series of readily available enaminones under Vilsmeier conditions is described, and a mechanism involving sequential halogenation, formylation, and intramolecular nucleophilic cyclization is proposed.
Similar articles
-
A facile and efficient synthesis of polyfunctionalized pyridin-2(1H)-ones from beta-oxo amides under Vilsmeier conditions.Org Lett. 2008 Jan 17;10(2):345-8. doi: 10.1021/ol702846t. Epub 2007 Dec 28. Org Lett. 2008. PMID: 18161982
-
Vilsmeier-Haack reactions of 2-arylamino-3-acetyl-5,6-dihydro-4H-pyrans toward the synthesis of highly substituted pyridin-2(1H)-ones.J Org Chem. 2007 Oct 26;72(22):8593-6. doi: 10.1021/jo7015482. Epub 2007 Oct 4. J Org Chem. 2007. PMID: 17915930
-
Efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones via the Vilsmeier-Haack reaction of 1-acetyl,1-carbamoyl cyclopropanes.Org Lett. 2007 Jun 7;9(12):2421-3. doi: 10.1021/ol070905i. Epub 2007 May 16. Org Lett. 2007. PMID: 17503843
-
Recent advances in heterobimetallic palladium(II)/copper(II) catalyzed domino difunctionalization of carbon-carbon multiple bonds.Org Biomol Chem. 2014 Sep 21;12(35):6767-89. doi: 10.1039/c4ob00610k. Org Biomol Chem. 2014. PMID: 25070146 Review.
-
Microwaves in drug discovery and multi-step synthesis.Mol Divers. 2003;7(2-4):273-80. doi: 10.1023/b:modi.0000006860.56083.2b. Mol Divers. 2003. PMID: 14870858 Review.
Cited by
-
A Stereodivergent Approach for Accessing Both C2,8a-Syn and C2,8a-Anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCL(4)-Promoted Aza-[3 + 3] Annulation.Synthesis (Stuttg). 2009 Sep 1;2009(17):2905. doi: 10.1055/s-0029-1216920. Synthesis (Stuttg). 2009. PMID: 20151022 Free PMC article.
-
An efficient method for the construction of polysubstituted 4-pyridones via self-condensation of β-keto amides mediated by P2O5 and catalyzed by zinc bromide.Beilstein J Org Chem. 2013 Nov 28;9:2681-7. doi: 10.3762/bjoc.9.304. eCollection 2013. Beilstein J Org Chem. 2013. PMID: 24367433 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources