Diels-Alder reactions of arylethenes. Synthesis of some [5]phenacenes and fluorenoanthracenes

Lucio Minuti, Aldo Taticchi, E. Gács-Baitz, Assunta Marrocchi

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

A one-pot high yielding route to 3,4-dihydro-1-(2H)-anthracenone (9) based on high pressure Diels-Alder reaction is described. The synthesis of 3,4-dihydro-1-vinylphenanthrene (1) and 3,4-dihydro-1-vinylanthracene (2) is reported. A new synthetic two-step approach to [5]phenacenes and fluorenoanthracenes has been developed. It is based on the Diels-Alder reaction of arylethenes 1 and 2 with benzyne (13), 1,4-benzoquinone (14), 1,4-naphthoquinone (15) and inden-1-one (17) and on the aromatization of the cycloadducts. Structure analysis of the reaction products by 1H and 13C- NMR spectroscopy is presented.

Original languageEnglish
Pages (from-to)10891-10898
Number of pages8
JournalTetrahedron
Volume54
Issue number36
Publication statusPublished - Sep 3 1998

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Aromatization
Cycloaddition Reaction
Reaction products
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Pressure
benzyne
1,4-naphthoquinone
benzoquinone
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Diels-Alder reactions of arylethenes. Synthesis of some [5]phenacenes and fluorenoanthracenes. / Minuti, Lucio; Taticchi, Aldo; Gács-Baitz, E.; Marrocchi, Assunta.

In: Tetrahedron, Vol. 54, No. 36, 03.09.1998, p. 10891-10898.

Research output: Contribution to journalArticle

Minuti, L, Taticchi, A, Gács-Baitz, E & Marrocchi, A 1998, 'Diels-Alder reactions of arylethenes. Synthesis of some [5]phenacenes and fluorenoanthracenes', Tetrahedron, vol. 54, no. 36, pp. 10891-10898.
Minuti, Lucio ; Taticchi, Aldo ; Gács-Baitz, E. ; Marrocchi, Assunta. / Diels-Alder reactions of arylethenes. Synthesis of some [5]phenacenes and fluorenoanthracenes. In: Tetrahedron. 1998 ; Vol. 54, No. 36. pp. 10891-10898.
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