Access to polysubstituted naphthalenes and anthracenes via a retro-Diels-Alder reaction

Akin E. T., Erdoğan M., Daştan A., SARAÇOĞLU N.

TETRAHEDRON, cilt.73, sa.37, ss.5537-5546, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 73 Sayı: 37
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.tet.2017.07.058
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.5537-5546
  • Anahtar Kelimeler: Tetrazine, retro-Diels-Alder, Naphthalene, Anthracene, BASE INDUCED CYCLOADDITION, VERSATILE BUILDING-BLOCK, SUBSTITUTED NAPHTHALENES, REGIOSELECTIVE SYNTHESIS, HOMOPHTHALIC ANHYDRIDES, REGIOSPECIFIC SYNTHESIS, FULVENE ENDOPEROXIDES, POLYCYCLIC STRUCTURES, DERIVATIVES, GENERATION
  • Atatürk Üniversitesi Adresli: Evet

Özet

Naphthalene and anthracene nuclei are present in several natural and synthetic compounds. Due to their unique physical and chemical properties, access to functionalized naphthalenes and anthracenes has attracted the attention of both synthetic and medicinal chemists over the decades. In this study, successive Diels Alder/retro-Diels Alder reactions of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with various bicyclic alkenes in one pot to yield naphthalene and anthracene derivatives are reported. Using anti- and syn-cyclotrimers derived from the cyclotrimerization of benzobarrelene as alkene partner enabled efficient synthesis of trinaphthylene. (C) 2017 Elsevier Ltd. All rights reserved.