New generation and intramolecular Diels-Alder reaction of isobenzofurans: an efficient furan ring-transfer reaction and a synthetic entry into the polycyclic ring systems

1987 ◽  
Vol 52 (10) ◽  
pp. 2040-2046 ◽  
Author(s):  
Yasuchika Yamaguchi ◽  
Hiromi Yamada ◽  
Kenji Hayakawa ◽  
Ken Kanematsu
Keyword(s):  
Transfer Reaction ◽  
Furan Ring ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ring Systems ◽  
Diels Alder Reaction ◽  
New Generation

scholarly journals NbCl5 as Catalyst in Diels-Alder Reaction of Furan Ring

2013 ◽  
Author(s):  
Deborah A. dos Santos ◽  
Ludmila R. Rodrigues ◽  
Valdemar Lacerda Jr. ◽  
Sandro J. Greco ◽  
Alvaro C. Neto ◽  
...  
Keyword(s):  
Furan Ring ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

scholarly journals Synthetic approaches to haplophytine. 2. Synthesis of 4-methylamino-1-(2-furanyl)-2-phenyl-2-(2-pivaloylamidophenyl)butan-1-one

1983 ◽  
Vol 61 (6) ◽  
pp. 1126-1131 ◽  
Author(s):  
David Aaron Schwartz ◽  
Peter Yates
Keyword(s):  
Furan Ring ◽  
Alder Reaction ◽  
Diels Alder ◽  
Acid Moiety ◽  
Diels Alder Reaction ◽  
Synthetic Approaches

Approaches to the synthesis of compounds related to the 7-aryl-7-[3-(1-hydroxy-2-aminophenyl)]-9-methylamino-5,6-dioxononanoic acid moiety (3) of the alkaloid haplophytine and its dihydrobromide are described. Treatment of the dianion of phenyl (o-pivaloylamidophenyl)methane with 2-furancarboxaldehyde followed by oxidation of the resulting alcohol gives 1-(2-furanyl)-2-phenyl-2-(2-pivaloylamidophenyl)ethanone (14). This on allylation gives 1-allyloxy-1-(2-furanyl)-2-phenyl-2-(2-pivaloylamidophenyl)ethene (20), which on being heated at 80–95 °C undergoes an intramolecular Diels–Alder reaction. Heating the resulting product or 20 at 165 °C converts them to the C-allylation product of 14, 1-(2-furanyl)-2-phenyl-2-(2-pivaloylamidophenyl)pent-4-en-1-one (22). Oxidation of 22 gives 4-(2-furoyl)-1,2,3,4-tetrahydro-4-phenyl-1-pivaloyl-2-quinolinol, which on Borch reduction gives 4-methylamino-1-(2-furanyl)-2-phenyl-2-(2-pivaloylamidophenyl)butan-1-one (24) and 2-(2-furanyl)-1-methyl-3-phenyl-3-(2-pivaloylamidophenyl)pyrrolidine. Compound 24 is a potential advanced intermediate for the synthesis of compounds related to 3. Experiments directed to the incorporation of a methoxyl or methylthio substituent at the C-5 position of the furan ring of 24 are also described.

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