Synthesis and mutagenicity of some benzo[g]- and indeno[a]phenanthrenes

Lucio Minuti, Aldo Taticchi, Assunta Marrocchi, Guido Morozzi, Lucia Pampanella, E. Gács-Baitz

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The synthesis of two aromatic ketones 7(H)-indeno[2,1-a]phenanthren-7-one and 11(H)-indeno[1,2-a]phenanthren-11-one by Diels-Alder cycloaddition of 1-vinyl-3,4-dihydro-naphthalene with inden-1-one generated in situ from 3-bromo-indan-1-one and triethylamine, followed by dehydrogenation-aromatization reaction of the cycloadducts, is reported. Further the synthesis of 7(H)-indeno[2,1-a]phenanthrene, 11(H)-indeno[1,2-a]phenanthrene, 9(H)-benzo[g]indeno[2,1-a]phenanthrene and 13(H)-benzo[g]indeno[1,2-a]phenanthrene by a procedure based on the reduction of the corresponding cycloadducts followed by a dehydration-aromatization reaction is presented. The assignments of the structure by 1H- and 13C-NMR spectroscopy is discussed. Estimates of the mutagenic activity of the compounds in Salmonella typhymurium determined by Ames' test show that three compounds are mutagenic for TA 98 strain and four for TA 100 strain. The mutagenic activities exhibited by these compounds are compared with those shown by cyclopenta[a]phenanthrenes. The effect of benzoannulation on cyclopenta[a]phenanthrenes and related cyclopenta[a]phenanthrenones is discussed.

Original languageEnglish
Pages (from-to)9-24
Number of pages16
JournalPolycyclic Aromatic Compounds
Volume13
Issue number1
Publication statusPublished - 1999

Fingerprint

Phenanthrenes
Aromatization
Salmonella
Cycloaddition
Dehydrogenation
Naphthalene
Ketones
Dehydration
Nuclear magnetic resonance spectroscopy
phenanthrene

Keywords

  • Benzo[g]phenanthrenes
  • Indeno[a]phenanthrenes
  • Mutagenicity
  • Synthesis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Minuti, L., Taticchi, A., Marrocchi, A., Morozzi, G., Pampanella, L., & Gács-Baitz, E. (1999). Synthesis and mutagenicity of some benzo[g]- and indeno[a]phenanthrenes. Polycyclic Aromatic Compounds, 13(1), 9-24.

Synthesis and mutagenicity of some benzo[g]- and indeno[a]phenanthrenes. / Minuti, Lucio; Taticchi, Aldo; Marrocchi, Assunta; Morozzi, Guido; Pampanella, Lucia; Gács-Baitz, E.

In: Polycyclic Aromatic Compounds, Vol. 13, No. 1, 1999, p. 9-24.

Research output: Contribution to journalArticle

Minuti, L, Taticchi, A, Marrocchi, A, Morozzi, G, Pampanella, L & Gács-Baitz, E 1999, 'Synthesis and mutagenicity of some benzo[g]- and indeno[a]phenanthrenes', Polycyclic Aromatic Compounds, vol. 13, no. 1, pp. 9-24.
Minuti L, Taticchi A, Marrocchi A, Morozzi G, Pampanella L, Gács-Baitz E. Synthesis and mutagenicity of some benzo[g]- and indeno[a]phenanthrenes. Polycyclic Aromatic Compounds. 1999;13(1):9-24.
Minuti, Lucio ; Taticchi, Aldo ; Marrocchi, Assunta ; Morozzi, Guido ; Pampanella, Lucia ; Gács-Baitz, E. / Synthesis and mutagenicity of some benzo[g]- and indeno[a]phenanthrenes. In: Polycyclic Aromatic Compounds. 1999 ; Vol. 13, No. 1. pp. 9-24.
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