scholarly journals A Novel One-step Synthesis of Quinoline-2(1H)-thiones and Selones by Treating 3-Aryl-3-(2-aminophenyl)-1-propyn-3-ols with a Base and Elemental Sulfur or Selenium

2015 ◽  
Vol 10 (6) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Kazuaki Shimada ◽  
Hironori Izumi ◽  
Koki Otashiro ◽  
Kensuke Noro ◽  
Shigenobu Aoyagi ◽  
...  

A one-step conversion of 3-aryl-3-(2-aminophenyl)-1-propyn-3-ols into quinoline-2(1 H)-thiones and quinoline-2(1 H)-selones was achieved only by treating the substrates with n-butyllithium and either elemental sulfur or selenium, respectively. The reactions were assumed to proceed through an intramolecular nucleophilic attack of the neighboring amino group to the plausible in situ generated reactive species related to chalcogenoketenes. The subsequent mCPBA oxidation of quinoline-2(1 H)-selones afforded quinolin-2(1 H)-ones in high yields.

2016 ◽  
Vol 113 (28) ◽  
pp. 7722-7726 ◽  
Author(s):  
Gavin O. Jones ◽  
Alexander Yuen ◽  
Rudy J. Wojtecki ◽  
James L. Hedrick ◽  
Jeannette M. García

It is estimated that ∼2.7 million tons poly(carbonate)s (PCs) are produced annually worldwide. In 2008, retailers pulled products from store shelves after reports of bisphenol A (BPA) leaching from baby bottles, reusable drink bottles, and other retail products. Since PCs are not typically recycled, a need for the repurposing of the PC waste has arisen. We report the one-step synthesis of poly(aryl ether sulfone)s (PSUs) from the depolymerization of PCs and in situ polycondensation with bis(aryl fluorides) in the presence of carbonate salts. PSUs are high-performance engineering thermoplastics that are commonly used for reverse osmosis and water purification membranes, medical equipment, as well as high temperature applications. PSUs generated through this cascade approach were isolated in high purity and yield with the expected thermal properties and represent a procedure for direct conversion of one class of polymer to another in a single step. Computational investigations performed with density functional theory predict that the carbonate salt plays two important catalytic roles in this reaction: it decomposes the PCs by nucleophilic attack, and in the subsequent polyether formation process, it promotes the reaction of phenolate dimers formed in situ with the aryl fluorides present. We envision repurposing poly(BPA carbonate) for the production of value-added polymers.


2017 ◽  
Vol 12 (6) ◽  
pp. 1934578X1701200
Author(s):  
Kazuaki Shimada ◽  
Fumiya Ishikawa ◽  
Md. Ashraful Alam ◽  
Toshinobu Korenaga

Treatment of substituted propargyl methyl ethers with a base and elemental sulfur in the presence of a thiolate ion afforded 2-alkenecarbodithioate esters in good yields. The reaction is assumed to proceed through a pathway involving in situ generation of propadienethione intermediates. Further conversion of 2-alkenecarbodithioate esters into 2,3-dihydroisothiazoles were efficiently performed by treating with chloramine-T through a [4+1] type oxidative ring closure via thiocarbonyl S-tosylimides.


2020 ◽  
Author(s):  
Cheng Li-Jie ◽  
Zhao Siling ◽  
Neal Mankad

A Cu-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in-situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.<br>


RSC Advances ◽  
2016 ◽  
Vol 6 (74) ◽  
pp. 70704-70714 ◽  
Author(s):  
Nan Li ◽  
Zuoqiang Wu ◽  
Lei Huo ◽  
Lishuai Zong ◽  
Yujie Guo ◽  
...  

In the present study, we developed a novel approach to introduce amino group (–NH2), hydroxyl group (–OH) and sulfhydryl group (–SH) onto carbon fibers (CFs) using aromatic diazonium salts.


Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7276
Author(s):  
Assem Barakat ◽  
Matti Haukka ◽  
Saied M. Soliman ◽  
Mohammad Ali ◽  
Abdullah Mohammed Al-Majid ◽  
...  

Straightforward regio- and diastereoselective synthesis of bi-spirooxindole-engrafted rhodanine analogs 5a–d were achieved by one-pot multicomponent [3 + 2] cycloaddition (32CA) reaction of stabilized azomethine ylide (AYs 3a–d) generated in situ by condensation of L-thioproline and 6-chloro-isatin with (E)-2-(5-(4-chlorobenzylidene)-2,4-dioxothiazolidin-3-yl)-N-(2-morpholinoethyl)acetamide. The bi-spirooxindole-engrafted rhodanine analogs were constructed with excellent diastereo- and regioselectivity along with high chemical yield. X-ray crystallographic investigations for hybrid 5a revealed the presence of four contiguous stereocenters related to C11, C12, C19 and C22 of the spiro structure. Hirshfeld calculations indicated the presence of many short intermolecular contacts such as Cl...C, S...S, S...H, O...H, N...H, H...C, C...C and H...H interactions. These contacts played a very important role in the crystal stability. The polar nature of the 32CA reaction was studied by analysis of the conceptual DFT reactivity indices. Theoretical study of this 32CA reaction indicated that it takes place through a non-concerted two-stage one-step mechanism associated with the nucleophilic attack of AY 3a to the electrophilic ethylene derivative.


2020 ◽  
Author(s):  
Cheng Li-Jie ◽  
Zhao Siling ◽  
Neal Mankad

A Cu-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in-situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.<br>


2021 ◽  
Vol 326 ◽  
pp. 129007
Author(s):  
Zahra Nasri ◽  
Giuliana Bruno ◽  
Sander Bekeschus ◽  
Klaus-Dieter Weltmann ◽  
Thomas von Woedtke ◽  
...  

Author(s):  
Liang Fang ◽  
Yanping Xie ◽  
Peiyin Guo ◽  
Jingpei Zhu ◽  
Shuhui Xiao ◽  
...  

Vertical NiPS3 nanosheets in situ grown on conducting nickel foam were fabricated by a facile one-step chemical vapor transport method and used as an efficient bifunctional catalyst for overall water splitting.


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