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Synthesis 1991; 1991(2): 159-161
DOI: 10.1055/s-1991-26404
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1,2,4-Benzothiadiazine 1,1-Dioxides, Part 4: Mitsunobu Reactions of 3-Hydroxyalkylamino- and 3-Mercaptoalkylamino-4H1, 2,4-benzothiadiazine 1,1-Dioxides. A Convenient Synthesis of Built-in Guanidine Tricycles and Disulfides

Ji-Wang Chern* , Chia-Yang Shiau, Ying-Hwa Wu
  • *Institute of Pharmacy and Medical Laboratories, National Defense Medical Center, P. O. Box 90048-512, Taipei, (10700), Taiwan, Republic of China
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Publication Date:
27 September 2002 (online)

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3-(2-Hydroxyethyl)amino- and 3-(3-hydroxypropyl)amino-4H-1,2,4-benzothiadiazine 1,1-dioxides (1a, b) were treated with triphenylphosphine in the presence of diethyl azodicarboxylate leading to the formation of 2,4-dihydro-1H-imidazo[2,1-c] [1,2,4]benzothiadiazine 5,5-dioxide (3a) and 1,2,3,5-tetrahydropyrimido[2,1-c][1,2,4]benzothiadiazine 6,6-dioxide (3b) in 94 % and 60 % yield, respectively. However, under the same conditions, the oxidized products bis[2-(1,1-dioxo-4H-1,2,4-benzothiadiazin-3-ylamino)ethyl] disulfide (6a) and bis[2-(1,1-dioxo-4H-1,2,4-benzothiadiazin-3-ylamino)propyl] disulfide (6b) were obtained from 3-(2-mercaptoethyl)amino- and 3-(3-mercaptopropyl)amino-4H-1,2,4-benzothiadiazine 1,1-dioxides (5a, b)