Facile and Efficient Synthesis of 7,10-Dihydroxy-6H-pyrazolo[4,5,1-de]acridin-6-one via Hypervalent Iodine Oxidation

Nobuyuki Kato; Toru Sugaya; Takashi Mimura; Masanori Ikuta; Sachiko Kato; Yukihiro Kuge; Shinji Tomioka; Masaji Kasai

doi:10.1055/s-1997-1398

Synthesis 1997; 1997(6): 625-627
DOI: 10.1055/s-1997-1398

short paper

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Facile and Efficient Synthesis of 7,10-Dihydroxy-6H-pyrazolo[4,5,1-de]acridin-6-one via Hypervalent Iodine Oxidation

Nobuyuki Kato^* , Toru Sugaya, Takashi Mimura, Masanori Ikuta, Sachiko Kato, Yukihiro Kuge, Shinji Tomioka, Masaji Kasai

^*Sakai Research Laboratories, Kyowa Hakko Kogyo Co., Ltd., 1-1-53 Takasucho, Sakai, Osaka 590, Japan, Fax +81(722)277214

Abstract

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An improved synthetic procedure for 5,8-dibromo-7,10-dihydroxy-2-methyl-6H-pyrazolo[4,5,1-de]acridin-6-one (4), an intermediate of a novel class of antitumor agents, was developed. An effective introduction of a hydroxy group to the C10 of 5,8-dibromo-7-hydroxy-2-methyl-6H-pyrazolo[4,5,1-de]acridin-6-one (2b) was accomplished in two steps via the oxidation of 2b to the corresponding quinone using hypervalent iodine reagent in an acidic medium, followed by reduction of the resulting quinone upon treatment with aqueous sodium hydrosulfite.

pyrazoloacridine derivative - hypervalent iodine oxidation - quinone intermediate of antitumor agent - fused heterocyclic compound

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