135067-69-5Relevant articles and documents
Iodine/persulfate-promoted site-selective direct thiolation of quinolones and uracils
Beukeaw, Danupat,Noikham, Medena,Yotphan, Sirilata
, (2019)
A simple and general method for direct thiolation of 4-quinolones with disulfides or thiols under I2/K2S2O8 system has been developed. Under the optimal conditions, the C–S bond coupling can take place effectively with good to decent yields and excellent regioselectivity of the S-linked products. The established metal-free site-selective approach was also applicable to transform a range of uracil substrates to the thio-substituted products under mild conditions. Further transformation to the sulfone derivatives can be conveniently performed in one-pot. These easy-to-handle protocols represent a useful and interesting synthetic alternative with good substrate scope and functional group compatibility.
Practical and sustainable approach for clean preparation of 5-organylselanyl uracils
Chen, Jin-Yang,Zhong, Chun-Tao,Gui, Qing-Wen,Zhou, Yuan-Ming,Fang, Yang-Yang,Liu, Kai-Jian,Lin, Ying-Wu,Cao, Zhong,He, Wei-Min
, p. 475 - 479 (2021)
An eco-friendly, sustainable and practical method for the efficient preparation of 5-organylselanyl uracils through the electrochemical selenylation of uracils and diorganyl diselenides at room temperature under oxidant- and external electrolyte-free cond
Method for preparing 5-sulfur/selenium-modified uracil derivative
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Paragraph 0225-0230, (2019/05/02)
The invention belongs to the field of organic chemistry and particularly relates to a method for efficiently preparing a 5-sulfur/selenium-modified uracil derivative. The method comprises the steps ofenabling a thiophenol compound shown as a formula I or
A NaI/H2O2-Mediated Sulfenylation and Selenylation of Unprotected Uracil and Its Derivatives
Li, Xue-Dong,Gao, Yu-Ting,Sun, Ying-Jie,Jin, Xiao-Yang,Wang, Dong,Liu, Li,Cheng, Liang
supporting information, p. 6643 - 6647 (2019/09/07)
An efficient iodide-catalyzed/hydrogen peroxide mediated sulfenylation and selenylation of unprotected uracil and its derivatives with simple thiols and diselenides was established. This coupling tolerates a broad variety of functional groups to provide d
Copper-Catalyzed Regioselective Direct C–H Thiolation and Thiocyanation of Uracils
Noikham, Medena,Yotphan, Sirilata
, p. 2759 - 2766 (2019/04/08)
A novel copper-catalyzed direct C–H thiolation and thiocyanation of uracils using disulfides and thiocyanate salts respectively as coupling partners are described. These reactions enable the C–H bond cleavage and C–S bond formation to proceed efficiently under relatively mild conditions, providing useful methods for a preparation of a series of thio-substituted at the C5 position of uracil derivatives. These protocols exhibit several merits including simple experimental procedures, readily accessible substrates and reagents, broad scopes, high yields, and excellent regioselectivity. Preliminary mechanistic studies revealed that a radical pathway is likely to be involved.
Development of reactions of 6- and 5-substituted 1,3-dimethyluracils with dimethylsulfoxonium methylide
Norris, Peter,Shechter, Harold
, p. 7290 - 7298 (2007/10/03)
6-Chloro-1,3-dimethyluracil (1) reacts with dimethylsulfoxonium methylide (3, 2 equiv) to give sulfoxonium ylide 8 (51%). The structure of 8 is established spectroscopically and by its reactions with various electrophiles and electron-deficient olefins. Thus, 8 is converted by HCl to sulfoxonium chloride 7, which then yields the 6-(chloromethyl)uracil 17 by heating in acetonitrile. Ylide 8 undergoes deuterium exchange at the 5- position, at its methine carbon, and into its methyl groups attached to sulfur. Reaction of 8 with benzoyl chloride gives the highly substituted ylide 19 or the nucleophilic substitution products 17 and 18 depending on reaction conditions. Treatment of 8 with electron-deficient olefins yields 6- cyclopropyluracils 20-31. Many of the cyclopropyluracils have been converted to trans-1-(1,3-dimethyluracilyl)-2-vinylcyclopropanes and cycloheptenyluracils. Reactions of 5-substituted uracils 2 (Z = SOPh and SeOPh) with ylide 3 have been developed. 5-(Phenylsulfinyl)uracil 48 yields cyclothymine derivative 49; 5-phenylseleninyluracil 52 gives methylide 8 as the major product.
Efficient phenylsulfenylation and phenylselenenylation at the 5-position of uracil nucleosides with disulfide and diselenide mediated by [bis(trifluoroacetoxy)iodo] benzene
Roh, Kyoung Rok,Chang, Hye Kyung,Kim, Yong Hae
, p. 437 - 441 (2007/10/03)
A series of uracil nucleosides reacted with diphenyl disulfide or diphenyl diselenide in the presence of hypervalent iodine reagent, [bis(trifluoroacetoxy)iodo]benzene, in acetonitrile to give the corresponding C-5 phenylsulfenylated or phenylselenenylate
Direct regioselective arylsulfenylation and arylselenenylation at 5-position of uracils mediated by silver reagents
Lee, Chun Ho,Kim, Yong Hae
, p. 2401 - 2404 (2007/10/02)
Electrophilic additions of phenylsulfenyl chloride or phenylselenenyl chloride to a carbon-carbon double bond of C-5,6 region uracils in the presence of silver reagents such as Ag2O, AgBF4, or AgOCOCF3 directly gave the co
