Syntheses of thiopyrone and pyrone derivatives by photocyclization reaction of 3-aryl-2-([1]benzothien-3-yl)propenoic acids

Kenji Sasaki, Y. Satoh, T. Hirota, T. Nakayama, Y. Tominaga, R. N. Castle

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Naphtho[1,2-b][1]benzothiophene-6-carboxylic acids, 6H-benzo[b]naphtho[2,3-d]thiopyran-6-ones and 6H-benzo[b]naphtho[2,3-d]pyran-6-ones were synthesized in one step by the photocyclization reaction of 3-aryl-2-([1]benzothien-3-yl)propenoic acids. The photocyclization reaction did not occur when the 3-aryl group contained the electron-withdrawing nitro group. The assignment of the 1H and 13C nmr spectra of 6H-benzo[b]naphtho[2,3-d]thiopyran-6-one and 6H-benzo[b]naphtho[2,3-d]pyran-6-one by two-dimensional nmr methods is described. The difference between the chemical shift values of H12 for these two compounds is attributed to different molecular geometries.

Original languageEnglish
Pages (from-to)959-967
Number of pages9
JournalJournal of Heterocyclic Chemistry
Volume37
Issue number4
Publication statusPublished - 2000

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Pyrones
Pyrans
Derivatives
Acids
Chemical shift
Carboxylic Acids
Geometry
Electrons
thiopyran
benzothiophene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Syntheses of thiopyrone and pyrone derivatives by photocyclization reaction of 3-aryl-2-([1]benzothien-3-yl)propenoic acids. / Sasaki, Kenji; Satoh, Y.; Hirota, T.; Nakayama, T.; Tominaga, Y.; Castle, R. N.

In: Journal of Heterocyclic Chemistry, Vol. 37, No. 4, 2000, p. 959-967.

Research output: Contribution to journalArticle

Sasaki, Kenji ; Satoh, Y. ; Hirota, T. ; Nakayama, T. ; Tominaga, Y. ; Castle, R. N. / Syntheses of thiopyrone and pyrone derivatives by photocyclization reaction of 3-aryl-2-([1]benzothien-3-yl)propenoic acids. In: Journal of Heterocyclic Chemistry. 2000 ; Vol. 37, No. 4. pp. 959-967.
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AU - Tominaga, Y.

AU - Castle, R. N.

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