5925-50-8Relevant academic research and scientific papers
An Expeditious Route to trans-Configured Tetrahydrothiophenes Enabled by Fe(OTf)3-Catalyzed [3+2] Cycloaddition of Donor–Acceptor Cyclopropanes with Thionoesters
Matsumoto, Yohei,Nakatake, Daiki,Yazaki, Ryo,Ohshima, Takashi
supporting information, p. 6062 - 6066 (2018/03/28)
A synthetic route to trans-configured tetrahydrothiophenes (THTs) through Fe(OTf)3-promoted [3+2] cycloaddition of donor–acceptor cyclopropanes with thionoesters was developed. The cycloaddition proceeded in high yield with high diastereoselectivity, affording transient α-alkoxy THTs. Not only aromatic and aliphatic thionoesters, but also thionolactone were applicable to the present iron catalysis. Further transformation of the S,O-ketal functionality of the product was achieved in a highly trans diastereoselective manner. Moreover, the utility of our methodology was clearly demonstrated by the synthesis of enantioenriched trans-configured THTs.
Facile Synthesis of 2,5-Disubstituted Thiazoles from Terminal Alkynes, Sulfonyl Azides, and Thionoesters
Miura, Tomoya,Funakoshi, Yuuta,Fujimoto, Yoshikazu,Nakahashi, Junki,Murakami, Masahiro
supporting information, p. 2454 - 2457 (2015/05/27)
A sequential procedure for the synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and thionoesters is reported. A copper(I)-catalyzed 1,3-dipolar cycloaddition of terminal alkynes with sulfonyl azides affords 1-sulfonyl-1,2,3-triazoles, which then react with thionoesters in the presence of a rhodium(II) catalyst. The resulting 3-sulfonyl-4-thiazolines subsequently aromatize into the corresponding 2,5-disubstituted thiazoles by elimination of the sulfonyl group. (Chemical Equation Presented).
P4S10/dimethicone tandem: Efficient reagent for thionation of various aromatic amides and esters
Cho, Dongho,Ahn, Jiyoung,De Castro, Kathlia A.,Ahn, Hyunseok,Rhee, Hakjune
supporting information; experimental part, p. 5583 - 5588 (2010/10/02)
Organosulfur compounds are valuable because of their rich and varied chemistry especially in biological field. We report a new and efficient way for thionation of various aromatic amides and esters using P4S 10/ dimethicone tandem. The ease of handling and higher yield makes this protocol economical.
2,4-Disubstituted-5-acetoxythiazoles: useful intermediates for the synthesis of thiazolones and 2,4,5-trisubstituted thiazoles
Qiao,Dominique,Goodnow Jr.
, p. 3682 - 3686 (2008/09/20)
A variety of 2,4-disubstituted-5-acetoxythiazoles were prepared from the substituted methyl benzoates in good to moderate yields using a three-step sequence: (1) ester to thionoester conversion, (2) coupling with an amino acid, and (3) acetic anhydride me
New Synthesis and Some Reactions of Vinyl Arenecarbodithioates. Wittig Reaction of (Triphenylphosphonio)methyl Arenecarbodithioate Iodides
Ishida, Masaru,Kaga, Koh-ichi,Sato, Hiroyuki,Yokoi, Masato,Kato, Shinzi
, p. 1403 - 1410 (2007/10/02)
Wittig reaction of new phosphonium salts, (triphenylphosphonio)methyl arenecarbodithioate iodides, with variety of aldehydes gave the corresponding vinyl dithiocarboxylate with nucleophiles such as potassium alkoxide or alkanethiolate was investigated and found to give the thioacylated products in high yields.Ab initio molecular orbital calculations of the model compound vinyl dithioformate, are also discussed.
New Conversion of Esters to Ethers and Its Application to the Preparation of Furano-18-crown-6
Baxter, Steven L.,Bradshaw, Jerald S.
, p. 831 - 832 (2007/10/02)
Thionoesters which are readily prepared from esters can be desulfurized with Raney nickel to form the corresponding ethers.This new synthetic pathway to convert esters to ethers avoids many of the steric and functional limitations of known methods and appears to be a general method for this conversion.
