doi: 10.1248/cpb.49.893.
Diels-Alder cycloadditions of 2(1H)-quinolones having an electron-withdrawing group at the 3-position acting as dienophiles with dienes
Affiliations
- PMID: 11456098
- DOI: 10.1248/cpb.49.893
Item in Clipboard
Diels-Alder cycloadditions of 2(1H)-quinolones having an electron-withdrawing group at the 3-position acting as dienophiles with dienes
Chem Pharm Bull (Tokyo).
2001 Jul.
Free article
Abstract
Diels-Alder cycloadditions of 2(1H)-quinolones having an electron-withdrawing group at the 3-position with alkyl- and silyloxy-1,3-butadienes (2a,b) were carried out to give phenanthridones richly functionalized regio- or stereoselectively under conditions of atmospheric and high pressure. Furthermore, regioselectivity and chemoselectivity of 3-substituted 2(1H)-quinolones to 2a, b were examined using MO calculation.
Similar articles
-
Recent Progress in Nitro-Promoted Direct Functionalization of Pyridones and Quinolones.Molecules. 2020 Feb 5;25(3):673. doi: 10.3390/molecules25030673. Molecules. 2020. PMID: 32033284 Free PMC article. Review.
-
Diels-Alder reaction of 1,3-butadiene derivatives with 1-methyl-2(1H)-quinolones having an electron-withdrawing group at the 4-position.Chem Pharm Bull (Tokyo). 2001 Jul;49(7):900-4. doi: 10.1248/cpb.49.900. Chem Pharm Bull (Tokyo). 2001. PMID: 11456099
-
Synthesis of 5(6H)-phenanthridones using Diels-Alder reaction of 3-nitro-2(1H)-quinolones acting as dienophiles.Chem Pharm Bull (Tokyo). 2006 Feb;54(2):204-8. doi: 10.1248/cpb.54.204. Chem Pharm Bull (Tokyo). 2006. PMID: 16462064
-
Synthesis of phenanthridones using Diels-Alder reactions of 4-substituted 2(1H)-quinolones acting as dienophiles.Chem Pharm Bull (Tokyo). 2001 Apr;49(4):407-12. doi: 10.1248/cpb.49.407. Chem Pharm Bull (Tokyo). 2001. PMID: 11310666
-
Electron-deficient 1- and 2-azabuta-1,3-dienes: a comprehensive survey of their synthesis and reactivity.Chem Soc Rev. 2011 Sep;40(9):4708-39. doi: 10.1039/c1cs15070g. Epub 2011 Jun 7. Chem Soc Rev. 2011. PMID: 21655551 Review.
Cited by
-
Chemistry of nitroquinolones and synthetic application to unnatural 1-methyl-2-quinolone derivatives.Molecules. 2010 Jul 30;15(8):5174-95. doi: 10.3390/molecules15085174. Molecules. 2010. PMID: 20714294 Free PMC article. Review.
-
Recent Progress in Nitro-Promoted Direct Functionalization of Pyridones and Quinolones.Molecules. 2020 Feb 5;25(3):673. doi: 10.3390/molecules25030673. Molecules. 2020. PMID: 32033284 Free PMC article. Review.
-
Catalytic Enantioselective Birch-Heck Sequence for the Synthesis of Phenanthridinone Derivatives with an All-Carbon Quaternary Stereocenter.J Org Chem. 2022 Jan 21;87(2):1154-1172. doi: 10.1021/acs.joc.1c02523. Epub 2022 Jan 5. J Org Chem. 2022. PMID: 34985891 Free PMC article.
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
