Efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones via the Vilsmeier-Haack reaction of 1-acetyl,1-carbamoyl cyclopropanes
- PMID: 17503843
- DOI: 10.1021/ol070905i
Efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones via the Vilsmeier-Haack reaction of 1-acetyl,1-carbamoyl cyclopropanes
Abstract
A facile and efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones is developed via the Vilsmeier-Haack reaction of readily available 1-acetyl,1-carbamoyl cyclopropanes, and a mechanism involving sequential ring-opening, haloformylation, and intramolecular nucleophilic cyclization reactions is proposed.
Similar articles
-
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
-
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
-
Efficient three-component one-pot synthesis of fully substituted pyridin-2(1H)-ones via tandem Knoevenagel condensation-ring-opening of cyclopropane-intramolecular cyclization.Chem Commun (Camb). 2009 Jun 28;(24):3636-8. doi: 10.1039/b905742k. Epub 2009 May 13. Chem Commun (Camb). 2009. PMID: 19521633
-
Synthetic applications of chiral 2,3-dihydro-4-pyridones.Curr Opin Drug Discov Devel. 2002 Nov;5(6):870-80. Curr Opin Drug Discov Devel. 2002. PMID: 12478718 Review.
-
The cyclopropene pyrolysis story.Chem Soc Rev. 2005 Aug;34(8):714-32. doi: 10.1039/b310975p. Epub 2005 Jun 14. Chem Soc Rev. 2005. PMID: 16186900 Review.
Cited by
-
An efficient tandem approach for the synthesis of functionalized 2-pyridone-3-carboxylic acids using three-component reaction in aqueous media.Mol Divers. 2014 Aug;18(3):535-43. doi: 10.1007/s11030-014-9522-x. Epub 2014 May 4. Mol Divers. 2014. PMID: 24792225
-
One-Flask Synthesis of Pyrazolo[3,4-d]pyrimidines from 5-Aminopyrazoles and Mechanistic Study.Molecules. 2017 May 16;22(5):820. doi: 10.3390/molecules22050820. Molecules. 2017. PMID: 28509884 Free PMC article.
-
Efficient and divergent synthesis of polyfunctionalized 2-pyridones from β-keto amides.RSC Adv. 2018 Oct 1;8(59):33625-33630. doi: 10.1039/c8ra05709e. eCollection 2018 Sep 28. RSC Adv. 2018. PMID: 35548816 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources