3989-48-8Relevant academic research and scientific papers
A straightforward synthesis of 5-sulfonamidomethyl substituted 4,7-dihydroazolo[1,5-a]pyrimidines
Shvets, Elena H.,Pidvorotnia, Anastasiia V.,Kulyk, Olesia G.,Mazepa, Alexander V.,Kolosov, Maksim A.
supporting information, p. 114 - 122 (2020/10/02)
4,7-Dihydroazolo[1,5-a]pyrimidin-5-ylmethanesulfonamides are side-products of the three-component Biginelli-like reaction of aminoazoles, aldehydes and N,N-dialkyl-2-ketomethanesulfonamides. Herein, we report a straightforward synthesis of 5-sulfonamidomethyl substituted 4,7-dihydroazolo[1,5-a]pyrimidines by a two-component condensation of aminoazoles and N,N-dialkyl(cinnamoyl)methanesulfonamides in DMF at reflux. The starting N,N-dialkyl-2-ketomethanesulfonamides can be obtained by either lithiation of N,N-dialkylmethanesulfonamides and reaction with aldehydes followed by oxidation of the resulting alcohols or by Claisen condensation of N,N-dialkylmethanesulfonamides with the corresponding esters. The chemical structures of all synthesized compounds are supported by 1H and 13C NMR-spectroscopy, mass spectrometry and elemental analysis.
Functionalization of Piperidine Derivatives for the Site-Selective and Stereoselective Synthesis of Positional Analogues of Methylphenidate
Babl, Tobias,Davies, Huw M. L.,Liu, Wenbin,R?ther, Alexander,Reiser, Oliver
supporting information, (2020/03/23)
Rhodium-catalyzed C?H insertions and cyclopropanations of donor/acceptor carbenes have been used for the synthesis of positional analogues of methylphenidate. The site selectivity is controlled by the catalyst and the amine protecting group. C?H functionalization of N-Boc-piperidine using Rh2(R-TCPTAD)4, or N-brosyl-piperidine using Rh2(R-TPPTTL)4 generated 2-substitited analogues. In contrast, when N-α-oxoarylacetyl-piperidines were used in combination with Rh2(S-2-Cl-5-BrTPCP)4, the C?H functionalization produced 4-susbstiuted analogues. Finally, the 3-substituted analogues were prepared indirectly by cyclopropanation of N-Boc-tetrahydropyridine followed by reductive regio- and stereoselective ring-opening of the cyclopropanes.
PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
Sarkar, Debayan,Ghosh, Manoj Kumar,Rout, Nilendri
supporting information, p. 2360 - 2364 (2018/05/24)
A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral pool. The user friendly “trio” enables easy generation of these versatile sulfur analogues and the reaction condition employed depict an economic outline.
Highly enantioselective transfer hydrogenation of racemic α-substituted β-keto sulfonamides: Via dynamic kinetic resolution
Xiong, Zhichao,Pei, Chengfeng,Xue, Peng,Lv, Hui,Zhang, Xumu
supporting information, p. 3883 - 3886 (2018/04/20)
Highly enantioselective transfer hydrogenation of β-keto sulfonamides was developed via dynamic kinetic resolution using a chiral Ru(ii) catalyst with an azeotropic solution of HCO2H/Et3N as a hydrogen donor, affording α-substituted β-hydroxyl sulfonamides in good yields with excellent diastereo- and enantioselectivities. This method is featured with mild conditions, easy operation, and a broad substrate scope, which make it possible to find wide applications in the synthesis of natural products and biologically active compounds containing the α-substituted β-hydroxyl sulfonamide core.
DBN hexafluorophosphate salts as convenient sulfonylating and phosphonylating agents
Jones, Caroline S.,Bull, Steven D.,Williams, Jonathan M. J.
supporting information, p. 8452 - 8456 (2016/09/28)
Air-stable N-sulfonyl and N-phosphonyl DBN hexafluorophosphate salts have been synthesised under mild conditions as sulfonylating and phosphonylating agents. These salts are highly efficient in the sulfonylation and phosphonylation of a range of N- and O-nucleophiles to generate sulfonamides, sulfonate esters, phosphoramidates and phosphonate esters in good yields.
A useful Pd-catalyzed Negishi coupling approach to benzylic sulfonamide derivatives
Zhou, Gang,Ting, Pauline,Aslanian, Robert,Piwinski, John J.
experimental part, p. 2517 - 2520 (2009/05/26)
(Chemical Equation Presented) A mild catalytic system to access diversely functionalized benzylic sulfonamides has been developed. Palladium-catalyzed α-arylation by Negishi cross-coupling of sulfonamide-stabilized anions and a wide range of aryl iodides, bromides, and triflates constitutes a practical strategy for the synthesis of various benzylic sulfonamides.
Hepatoselectivity of statins: Design and synthesis of 4-sulfamoyl pyrroles as HMG-CoA reductase inhibitors
Park, William K.C.,Kennedy, Robert M.,Larsen, Scott D.,Miller, Steve,Roth, Bruce D.,Song, Yuntao,Steinbaugh, Bruce A.,Sun, Kevin,Tait, Bradley D.,Kowala, Mark C.,Trivedi, Bharat K.,Auerbach, Bruce,Askew, Valerie,Dillon, Lisa,Hanselman, Jeffrey C.,Lin, Zhiwu,Lu, Gina H.,Robertson, Andrew,Sekerke, Catherine
, p. 1151 - 1156 (2008/09/19)
4-Sulfamoyl pyrroles were designed as novel hepatoselective HMG-CoA reductase inhibitors (statins) to reduce myalgia, a statin-induced adverse effect. The compounds were prepared via a [3 + 2] cycloaddition of a Muenchnone with a sulfonamide-substituted alkyne. We identified compounds with greater selectivity for hepatocytes compared to L6-myocytes than rosuvastatin and atorvastatin. There was an inverse correlation of myocyte potencies and C log P values. A number of analogs were effective at reducing cholesterol in acute and chronic in vivo models but they lacked sufficient chronic in vivo activity to warrant further development.
Base-free monosulfonylation of amines using tosyl or mesyl chloride in water
Kamal, Ahmed,Reddy, J. Surendranadha,Bharathi, E. Vijaya,Dastagiri
, p. 348 - 353 (2008/09/17)
A mild and efficient procedure has been developed for the monosulfonylation of various amines using mesyl or tosyl chlorides in water at room temperature to afford the corresponding sulfonamides in high yields.
An easy microwave-assisted synthesis of sulfonamides directly from sulfonic acids
De Luca, Lidia,Giacomelli, Giampaolo
, p. 3967 - 3969 (2008/09/19)
(Chemical Equation Presented) An easy and handy synthesis of sulfonamides directly from sulfonic acids or its sodium salts is reported. The reaction is performed under microwave irradiation, has shown a good functional group tolerance, and is high yielding.
β-cyclodextrin-catalyzed monosulfonylation of amines and amino acids in water
Sridhar,Srinivas,Kumar, V. Pavan,Narender,Rao, K. Rama
, p. 1873 - 1876 (2008/09/16)
A mild and efficient procedure has been developed for the first time under biomimetic conditions for the monosulfonylation of various amines and amino acids catalyzed by β-cyclodextrin in water at room temperature to afford the corresponding sulfonamides in high yields.
