5656-61-1Relevant articles and documents
Furan Derivatives. IV. On the Effects of Substituents in the Syntheses of 4,5-Dihydro-3H-naphthofurans
Horaguchi, Sakaaki,Hara, Mamoru,Suzuki, Tsuneo
, p. 865 - 869 (1982)
The reaction of (8-oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetic acids with acetic anhydride and sodium acetate give a mixture of 4,5-dihydro-3H-naphthofurans and lactones.The relative yiels of 4,5-dihydro-3H-naphthofurans and lactones varied according to kinds of substituents on the benzene ring of (8-oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetic acids.Substituents which make the methylene group approach closer to the carbonyl carbon atom of (8-oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetic acids by a steric effect seem to favor the production of 4,5-dihydro-3H-naphthofurans.On the other hand, substituents which make the methylene group separate from the carbonyl carbon atom seem to favor the production of lactones.An electron-withdrawing chlorine atom on the benzene ring of (8-oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetic acids also favors the production of 4,5-dihydro-3H-naphthofurans.
Photocyclization Reactions. Part 4 [1]. Synthesis of Naphtho[1,8-bc]-furans and Cyclohepta[cd]benzofurans Using Photocyclization of Ethyl 2-(8-Oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetates and Ethyl 2-(5-Oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-4-yloxy)acetates
Sharshira, Essam Mohamed,Iwanami, Haruki,Okamura, Mutsuo,Hasegawa, Eietsu,Horaguchi, Takaaki
, p. 137 - 144 (2007/10/03)
Photocyclization reactions were carried out on ethyl 2-(8-oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetates 1a-e and ethyl 2-(5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-4-yloxy)acetates 2a-e in acetonitrile. Irradiation of 1a-e gave naphtho[1,8-bc]furanols 3a-e and naphtho[1,8-bc]furans 4a-e in 33-83% yields and ethyl acrylates 5b-d were produced in 3-25% yields during irradiation of 1b-d. On the other hand, 2a-e afforded cyclohepta[cd]benzofuranols 6a-e and cyclohepta[cd]benzofurans 7a-e in 44-87% yields. Ethyl acrylates 8b-d were also produced in 7-43% yields from irradiation of 2b-d. Substituent effects on photocyclization and reaction pathways are discussed.