Photocyclization reactions. Part 4  . 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‐5 H ‐benzocyclohepten‐4‐yloxy)acetates | Zendy

Sharshira Essam Mohamed | Zendy; Iwanami Haruki | Zendy; Okamura Mutsuo | Zendy; Hasegawa Eietsu | Zendy; Horaguchi Takaaki | Zendy

Premium

Photocyclization reactions. Part 4 . 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‐5 H ‐benzocyclohepten‐4‐yloxy)acetates

Author(s) -

Sharshira Essam Mohamed,

Iwanami Haruki,

Okamura Mutsuo,

Hasegawa Eietsu,

Horaguchi Takaaki

Publication year - 1996

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570330124

Subject(s) - chemistry , substituent , acetonitrile , medicinal chemistry , irradiation , stereochemistry , organic chemistry , physics , nuclear physics

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‐5 H ‐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[ ad |benzofuranols 6a‐e and cyclohepta[ ad ]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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research