4910-32-1Relevant academic research and scientific papers
Interrupted aza-Wittig reactions using iminophosphoranes to synthesize 11C-carbonyls
Ismailani, Uzair S.,Munch, Maxime,Mair, Braeden A.,Rotstein, Benjamin H.
supporting information, p. 5266 - 5269 (2021/06/06)
A direct CO2-fixation methodology couples structurally diverse iminophosphoranes with various nucleophiles to synthesize ureas, carbamates, thiocarbamates, and amides, and is amenable for 11C radiolabeling. This methodology is practical, as demonstrated by the synthesis of >35 products and isolation of the molecular imaging radiopharmaceuticals [11C]URB694 and [11C]glibenclamide. This journal is
N -Acylbenzotriazoles as Proficient Substrates for an Easy Access to Ureas, Acylureas, Carbamates, and Thiocarbamates via Curtius Rearrangement Using Diphenylphosphoryl Azide (DPPA) as Azide Donor
Yadav, Mangal S.,Singh, Sumt K.,Agrahari, Anand K.,Singh, Anoop S.,Tiwari, Vinod K.
, p. 2494 - 2502 (2021/03/26)
A diverse range of ureas, N -acylureas, carbamates, and thiocarbamates has been synthesized in good to excellent yields by reacting N -acylbenzotriazoles individually with amines or amides or phenols or thiols in the presence of diphenylphosphoryl azide (DPPA) as a suitable azide donor in anhydrous toluene at 110 °C for 3-4 hours. In this route, DPPA was found to be a good alternative to trimethylsilyl azide and sodium azide for the azide donor in Curtius degradation. The high reaction yields, one-pot and metal-free conditions, straightforward nature, easy handling, use of readily available reagents, and in many cases avoidance of column chromatography are the notable features of the devised protocol.
Synthesis of carbamothioate derivatives via a copper catalyzed thiocarboxamidation of aryl iodides
Khalaj, Mehdi
, p. 945 - 952 (2020/05/26)
Abstract: A catalytic route to carbamothioate derivatives through a reaction involving isocyanides, elemental sulfur, and aryl iodides has been developed. The reaction scope has been examined using a range of isocyanides and aryl iodides. The reactions involve two consecutive C–S bond formations. Control experiment revealed that the reaction proceeds through an iminium species. Graphic abstract: [Figure not available: see fulltext.].
Thermolysis-Induced Two- or Multicomponent Tandem Reactions Involving Isocyanides and Sulfenic-Acid-Generating Sulfoxides: Access to Diverse Sulfur-Containing Functional Scaffolds
Wu, Shengfeng,Lei, Xiaofang,Fan, Erkang,Sun, Zhihua
, p. 522 - 525 (2018/02/10)
Direct reaction of isocyanides with some sulfenic-acid-generating sulfoxides led to the effective formation of the corresponding thiocarbamic acid S-esters in good to high yields. A multicomponent reaction involving isocyanide, sulfoxide, and a suitable nucleophile has also been developed, providing ready access to a diverse range of sulfur-containing compounds, including isothioureas, carbonimidothioic acid esters, and carboximidothioic acid esters.
One-pot synthesis of carbamates and thiocarbamates from Boc-protected amines
Kim, Hee-Kwon,Lee, Anna
, p. 4890 - 4892 (2016/10/21)
A highly efficient one-pot procedure for the synthesis of carbamates and thiocarbamates has been described. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, the isocyanate intermediates were generated in situ for further reactions with alcohols and thiols to afford the desired carbamates and thiocarbamates in high yields.
Facile one-pot synthesis of unsymmetrical ureas, carbamates, and thiocarbamates from Cbz-protected amines
Kim, Hee-Kwon,Lee, Anna
supporting information, p. 7345 - 7353 (2016/08/05)
A novel one-pot synthesis of unsymmetrical ureas, carbamates and thiocarbamates from Cbz-protected amines has been developed. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, isocyanates are generated in situ, which facilitate rapid reaction with amines, alcohols, and thiols to afford the corresponding ureas, carbamates and thiocarbamates in high yields.
Synthesis of unsymmetrical ureas and S-thiocarbamates under catalyst-free conditions in a [BMIM]BF4 ionic liquid
Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Aghili, Nora
, p. 175 - 182 (2015/05/27)
Unsymmetrical ureas and Sthiocarbamates were prepared in good to excellent yields by direct condensation of phenylurea with amines and thiols in 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM]BF4) without the addition of any additives. The [BMIM]BF4 ionic liquid is a mild medium and can be recycled and reused several times.
Preparation of ionic liquid-based vilsmier reagent from novel multi-purpose dimethyl formamide-like ionic liquid and its application
Hullio, Ahmed Ali,Mastoi
, p. 1647 - 1657 (2012/09/21)
In continuation of research to explore the applied potential of DMF-like ionic liquid, the ionic liquid version of N,N-dimethyliminiumchloride (Vilsmier reagent) has been synthesized from DMF-like ionic liquid and tested effectively for its capacity to achieve more useful organic transformations. The results show that DMF-like ionic liquid is world's first task specific ionic liquid which has catalyzed numerous diverse type of reaction and is multipurpose in its application. Thus a new term for this DMF-like ionic liquid has been coined that is DMF-like "multipurpose" ionic liquid. Copyright
Cyclodimerization and cyclotrimerization of isocyanates promoted by one praseodymium benzenethiolate complex [Pr(SPh)3(THF)3]
Wang, He-Ming,Li, Hong-Xi,Yu, Xiang-Yang,Ren, Zhi-Gang,Lang, Jian-Ping
experimental part, p. 1530 - 1535 (2011/04/15)
The cyclotrimerization of aryl isocyanates and the cyclodimerization of alkyl isocyanates initiated by one praseodymium benzenethiolate complex [Pr(SPh)3(THF)3] were investigated. Comparative runs with [Pr(SPh)3(THF)3] and its precursor Pr[(Me 3Si)2N]3 showed that the former has the advantages of a higher selectivity toward isocyanates, easy preparation, low catalyst loading, high conversion as well as mild reaction conditions.
Thiol-isocyanate-ene ternary networks by sequential and simultaneous thiol click reactions
Shin, Junghwan,Matsushima, Hironori,Comer, Christopher M.,Bowman, Christopher N.,Hoyle, Charles E.
scheme or table, p. 2616 - 2625 (2011/11/13)
Thiol-isocyanate-ene ternary networks with systematic variations (100/100/0, 100/80/20, 100/60/40, 100/40/60, 100/20/80, and 100/0/100) were prepared by sequential and simultaneous thiol-ene and thiol-isocyanate click reactions. The thiol-isocyanate coupling reaction was triggered thermally or photolytically to control the sequence with the thiol-ene photopolymerization. Triethyl amine (TEA) and 2,2-dimethoxy-2-phenyl acetophenone (DMPA) were used for the sequential thermally induced thiol-isocyanate coupling and photochemically initiated thiol-ene reaction, respectively. A thermally stable photolatent base catalyst (tributylaminetetraphenylborate salt, TBAHBPh 4) capable of in situ generation of tributylamine by UV light was used with isopropylthioxanthone (ITX) for the simultaneous thiol-isocyanate/ thiol-ene curing systems. The kinetics of the hybrid networks investigated using real-time IR indicate that both thiol-isocyanate and thiol-ene reactions were quantitatively rapid and efficient (>90% of conversion in a matter of minutes and seconds, respectively). The Tg of the thiourethane/thiol-ene hybrid networks progressively increases (-5 to 35 °C by DSC) as a function of the thiourethane content due to the higher extent of hydrogen bonding, also resulting in enhanced mechanical properties. Highly uniform and dense network structures exhibiting narrow full width at half-maximum (~10 °C) were obtained for both the sequential and the simultaneous thiol click reactions, resulting in identical thermal properties that are independent of the sequence of the curing processes.
