491877-80-6Relevant academic research and scientific papers
Convenient method for the preparation of 1-phenylthio-3-alken-1-ynes and 4-hydroxy-1-phenylthio-1,2-alkadienes from a common precursor
Ogawa, Atsushi,Sakagami, Kazunari,Shima, Akiko,Suzuki, Hitoshi,Komiya, Satsuki,Katano, Yoshinori,Mitsunobu, Oyo
, p. 6387 - 6389 (2002)
4-Hydroxy-1-phenylthio-2-alkynes (5) reacted with dihydropyran to afford the corresponding 4-tetrahydropyranyloxy derivatives which, on treatment with KHMDS, gave a mixture of (E)- and (Z)-1-phenylthio-3-alken-1-ynes, with the former predominant. When MeLi was used in the place of KHMDS, the (Z)-isomers were formed in preference to the (E)-isomers. Further treatment of the mixture with a base converted the (Z)-isomers into (E)-isomers. On the other hand, the reaction of 5 with KHMDS gave the corresponding 4-hydroxy-1-phenythio-1,2-alkadienes.
Electrophilic cyclization of 4-thio-but-2-yn-1-ols via 1,2-migration of the thio group: efficient synthesis of 2,4-dihalo-3-thio-substituted furans
Zhou, Hongwei,Yao, Jinzhong,Liu, Guoliang
, p. 226 - 228 (2008/03/30)
A facile and efficient method for the synthesis of 2,4-dihalo-3-thio-furans via the electrophilic cyclization and 1,2-migration of the thio group of 4-thio-but-2-yn-1-ols was developed. As a result of the ready availability of starting materials and the s
Reduction of propargylic sulfones to (Z)-allylic sulfones using zinc and ammonium chloride
Sheldrake, Helen M.,Wallace, Timothy W.
, p. 4407 - 4411 (2008/02/03)
Propargylic sulfones can be cis-hydrogenated using commercial zinc powder and ammonium chloride in THF-water at room temperature, the major products being the corresponding (Z)-allylic sulfones. Other reducible groups (alkene, benzyloxy) are not affected. Allenylsulfones are implicated in one of the possible reaction pathways.
Iron(II)-catalyzed sulfimidation and [2,3]-sigmatropic rearrangement of propargyl sulfides with tert-butoxycarbonyl azide. Access to N-allenylsulfenimides
Bacci, James P.,Greenman, Kevin L.,Van Vranken, David L.
, p. 4955 - 4958 (2007/10/03)
The iron(II)-catalyzed Bach reaction of tert-butoxycarbonyl azide (BocN3) and allyl sulfides has been extended to include propargyl sulfides, which give N-allenylsulfenimide products. Using 10 mol % dppeFeCl2 as catalyst the reaction
DNA cleavage of novel propargylic sulfones. Enhancement of potency via intercalating interaction
Dai, Wei-Min,Fong, Kin Chiu,Danjo, Hiroshi,Nishimoto, Sei-Ichi,Solow, Michael,Mak, Wing Leung,Yeung, Mau Lam
, p. 1093 - 1098 (2007/10/03)
A number of novel hydroxy propargylic sulfones 7-15 were synthesized as DNA cleaving agents. Enhancement of DNA cleavage potency was observed with those compounds which could interact with DNA through intercalation of the extended aromatic rings.
