- Selective: S -arylation of 2-oxazolidinethiones and selective N -arylation of 2-benzoxazolinones/2-benzimidazolinones
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There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (CS). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes, it is found that N-arylation outcompetes O-arylation and aryne insertion into the CO group to give N-aryl 2-benzoxazolinones and N-aryl 2-benzimidazolinones.
- Sun, Chu-Han,Lu, Yi,Zhang, Qing,Lu, Rong,Bao, Lin-Qing,Shen, Mei-Hua,Xu, Hua-Dong
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supporting information
p. 4058 - 4063
(2017/07/10)
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- Thiocarbonyl Surrogate via Combination of Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione Construction
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An efficient and practical thiocarbonyl surrogate via combination of sulfur and chloroform has been developed. A variety of thiocarbamides and oxazolidinethiones have been established, including chiral thiourea catalysts and chiral oxazolidinethione auxiliaries with high selectivity. Meanwhile, pesticides Diafenthiuron (an acaricide), ANTU (a rodenticide), and Chloromethiuron (an insecticide) were practically synthesized through this method in gram scale. Dicholorocarbene, as the key intermediate, was further confirmed via a carbene-trapping control experiment.
- Tan, Wei,Wei, Jianpeng,Jiang, Xuefeng
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supporting information
p. 2166 - 2169
(2017/04/27)
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- Synthesis, X-ray analysis, and biological activities of novel oxazolidinethiones
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Oxazolidinethione compounds were synthesized starting from racemic and enantiopure β-amino alcohols. The molecular structure of oxazolidinethione 6a was elucidated by single-crystal x-ray crystallography. Oxazolidinethione compounds screened for antimicro
- Saygili, Nezire,?zalp, Meral,Yildirim, Leyla Tatar
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p. 1264 - 1269
(2015/04/27)
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- Thiophene-anthranilamides as highly potent and orally available factor Xa inhibitors
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There remains a high unmet medical need for a safe oral therapy for thrombotic disorders. The serine protease factor Xa (fXa), with its central role in the coagulation cascade, is among the more promising targets for anticoagulant therapy and has been the
- Ye, Bin,Arnaiz, Damian O.,Chou, Yuo-Ling,Griedel, Brian D.,Karanjawala, Rushad,Lee, Wheeseong,Morrissey, Michael M.,Sacchi, Kama L.,Sakata, Steven T.,Shaw, Kenneth J.,Wu, Shung C.,Zhao, Zuchun,Adler, Marc,Cheeseman, Sarah,Dole, William P.,Ewing, Janice,Fitch, Richard,Lentz, Dao,Liang, Amy,Light, David,Morser, John,Post, Joseph,Rumennik, Galina,Subramanyam, Babu,Sullivan, Mark E.,Vergona, Ron,Walters, Janette,Wang, Yi-Xin,White, Kathy A.,Whitlow, Marc,Kochanny, Monica J.
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p. 2967 - 2980
(2008/02/07)
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- Chemo-enzymatic preparation from renewable resources of enantiopure 1,3- oxazolidine-2-thiones
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Chiral 1,3-oxazolidine-2-thiones were prepared in enantiopure form from renewable resources through an enzymatic process involving immobilized myrosinase (thioglucoside glucohydrolase E.C. 3.2.3.1). (C) 2000 Elsevier Science Ltd.
- Leoni, Onofrio,Bernardi, Roberta,Gueyrard, David,Rollin, Patrick,Palmieri, Sandro
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p. 4775 - 4780
(2007/10/03)
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