3739-82-0Relevant academic research and scientific papers
Cs2CO3-Promoted C?O Coupling Protocol Enables Solventless (Hetero)aryl Ether Synthesis under Air Atmosphere
Jiang, Bowen,Chen, Cheng,Fan, Guang-Gao,Sang, Wei,Cheng, Hua,Zhang, Rui,Yuan, Ye,Li, Qi-Zhong,Verpoort, Francis
supporting information, (2022/02/05)
In this work, a Cs2CO3-promoted synthetic approach was identified for (hetero)aryl ether synthesis via the C?O coupling of various (hetero)aryl chlorides and alcohols/phenol. To our delight, the reactions could be carried out under transition-metal-free and solvent-free conditions. Moreover, analytical-grade reagents and air atmosphere were readily tolerated. To showcase the practical usefulness of the present protocol, the assembly of a bioactive molecule was facilely realized and the gram-scale production of selected ether products was also efficiently accomplished. In addition, density functional theory (DFT) studies, along with a few mechanistic experiments, were conducted to elucidate a proposed reaction pathway and rationalize the pivotal role of Cs2CO3 in promoting this process. Hopefully, this work could provide useful information for researchers who are engaging in C?O cross-coupling reactions.
Metal- And Oxidant-Free Electrochemical Oxidative Desulfurization C-O Coupling of Thiourea-Type Compounds with Alcohols
Cao, Bao-Qian,Quan, Zheng-Jun,Ren, Ming-Zhe,Wang, Xi-Cun,Zhu, Zheng-He
, p. 1634 - 1642 (2020/05/25)
An efficient desulfurization C-O coupling reaction of 3,4-dihydropyrimidine-2(1 H)-thiones (including thioureas) with alcohols was developed under electrochemical oxidation conditions. Herein, transition--metal catalysts and additives are not required and
Decyanative Cross-Coupling of Cyanopyrimidines with O-, S-, and N-Nucleophiles: A Route to Alkoxylpyrimidines, Aminopyrimidines and Alkylthiopyrimidines
Wei, Xiangyang,Zhang, Caiyang,Wang, Yifei,Zhan, Qi,Qiu, Guiying,Fan, Ling,Yin, Guodong
, p. 7142 - 7150 (2019/11/14)
The transition metal-free cross-coupling reactions of cyanopyrimidines with aliphatic alcohols, thiols (or S-alkylisothiourea salts) and amines, giving the corresponding alkoxylpyrimidines, aminopyrimidines, and alkylthiopyrimidines, are reported. Prelimi
Efficient nucleophilic substitution reactions of pyrimidyl and pyrazyl halides with nucleophiles under focused microwave irradiation
Cherng, Yie-Jia
, p. 887 - 890 (2007/10/03)
Rapid nucleophilic displacement reactions of 2-chloropyrimidine, 2-bromopyrimidine, 5-bromopyrimidine and chloropyrazine with nucleophiles under microwave irradiation was complete within several minutes with yields up to 99%. The method using microwave irradiation is superior to the classical heating processes.
The synthesis of bisguanidinoalkanes and guanidinoalkanes, N- or N′-substituted with pyrimidines, as analogues of chlorhexidine
Elmes, Bryan C.,Holan, George,Wernert, Gregory T.,Winkler, David A.
, p. 573 - 579 (2007/10/03)
A series of N,N?-alkanediylbis[N′-(5-halopyrimidin-2-yl)guanidine] salts has been synthesized along with N,N?-(trans-cyclohexane-1,4-diyl)bis[N′-(5-chloropyrimidin-2-yl) guanidine], N,N?-(ciscyclohexane-1,4-diyl)bis[N′-(5-chloropyrimidin-2-yl) guanidine]
Oxidation of substituted 2-thiouracils and pyrimidine-2-thione with ozone and 3,3-dimethyl-1,2-dioxirane
Claudia, Crestini,Mincione, Enrico,Saladino, Raffaele,Nicoletti, Rosario
, p. 3259 - 3272 (2007/10/02)
Ozone and 3,3-dimethyl-1,2-dioxirane react with substituted 2-thiouracils and pyrimidine-2-thione to afford several interesting desulfurized products. The effect of the solvent, protic as opposed to nonprotic, on the course of oxidation was striking.
Ozonation of substituted 2-thiouracils and pyrimidine-2-thione
Crestini, Claudia,Saladino, Raffaele,Nicoletti, Rosario
, p. 1631 - 1634 (2007/10/02)
The ozonation of substituted 2-thiouracils and pyrimidine-2-thione is reported; this provides a new method for the synthesis of several pyrimidine derivatives.
The Mechanism of Thermal Eliminations. Part 18. Relative Rates of Pyrolysis of 2-Ethoxypyrazine, 3-Ethoxypyridazine, 2-and 4-Ethoxypyrimidine, 3-Chloro-6-ethoxypyridazine, and 2-Chloro-4-ethoxypyrimidine : the Effect of the Aza 'Substituent' and ?-Bond Order on the Elimination Rate
Al-Awadi, Nouria,Taylor, Roger
, p. 1255 - 1258 (2007/10/02)
A kinetic study has been made of the first-order thermal decomposition of the title compounds into ethylene and the corresponding aza-substituted pyridines, between 650 and 713 K.The relative elimination rates at 650 K are (2-ethoxypyridine = 1): 0.545, 10.0, 1.03, 1.12, 9.68, and 3.28, respectively.The electronic effects of the aza 'substituent' are small, and a more important factor appears to be the C-N ?-bond order; this latter accounts for the high reactivity of the pyridazines.The effects of the chloro substituent and of the aza 'substituent' are explicable in terms of a balance between electron withdrawal from the C-O bond (producing deactivation) and from the nitrogen involved in the cyclic transition state (producing deactivation).The effects of the chloro substituents confirm that the most important step of the reaction is breaking of the C-O bond.The statistically corrected rate (per ring nitrogen) of 2-ethoxypyrimidine is unexpectedly low.This may reflect difficulty in achieving the coplanar transition state in which the lone pairs in the s-orbitals of oxygen and the nitrogen not involved in the elimination are brought into close proximity.
