A short and efficient synthesis of cytotoxic 3-isopropylnaphthalene-1,2-dione via 3-hydroxy-2-naphthoic acid

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BURMAOĞLU S., Altundas R., Secen H.

ARKIVOC, ss.269-273, 2008 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası:
  • Basım Tarihi: 2008
  • Doi Numarası: 10.3998/ark.5550190.0009.e24
  • Dergi Adı: ARKIVOC
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.269-273
  • Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
  • Erzincan Binali Yıldırım Üniversitesi Adresli: Hayır

Özet

3-Isopropylnaphthalene-1,2-dione (1) was synthesized from 3-hydroxy-2-naphthoic acid (5) in 4 steps (59% overall yield). After conversion of 5 to its methyl ester derivative, the crucial steps of the synthesis were the treatment of the ester with 4 eq MeMgI and then Pd-C catalyzed hydrogenation to give 3-isopropylnaphthalen-2-ol (8). Oxidation of 8 with m-chloroperbenzoic acid gave 1 in good yield.