61124-61-6Relevant academic research and scientific papers
Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones
Wei, Zeyang,Zhang, Qi,Tang, Meng,Zhang, Siyu,Zhang, Qian
supporting information, p. 4436 - 4440 (2021/05/26)
The diversity-oriented synthesis of 1,2,4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones was developed, and the reactions were general for a wide range of substrates, in which NH2CN, KOCN, KSCN, and KSeCN were used as odorless sources. Two different pathways were proposed, and N-tosylhydrazonoyl chlorides were formed in situ in the presence of NCS.
Iron Hydride Radical Reductive Alkylation of Unactivated Alkenes
Saladrigas, Mar,Bonjoch, Josep,Bradshaw, Ben
supporting information, p. 684 - 688 (2020/01/31)
Iron-catalyzed hydrogen atom transfer-mediated intermolecular C-C coupling reactions between alkenes and tosylhydrazones, followed by in situ cleavage of the tosylhydrazine intermediates using Et3N, are described. The process involves a new strategic bond disconnection resulting in the reductive alkylation of nonactivated alkenes. The reaction is operationally simple, proceeds under mild conditions, and has a wide substrate scope.
Divergent Synthesis of Vinyl-, Benzyl-, and Borylsilanes: Aryl to Alkyl 1,5-Palladium Migration/Coupling Sequences
Han, Jie-Lian,Ju, Cheng-Wei,Qin, Ying,Zhao, Dongbing
supporting information, p. 6555 - 6560 (2020/03/03)
Organosilicon compounds have been extensively utilized both in industry and academia. Studies on the syntheses of diverse organosilanes is highly appealing. Through-space metal/hydrogen shifts allow functionalization of C?H bonds at a remote site, which are otherwise difficult to achieve. However, until now, an aryl to alkyl 1,5-palladium migration process seems to have not been presented. Reported herein is the remote olefination, arylation, and borylation of a methyl group on silicon to access diverse vinyl-, benzyl-, and borylsilanes, constituting a unique C(sp3)?H transformation based on a 1,5-palladium migration process.
Acid-Promoted [3 + 1 + 1] Cyclization of N-Tosylhydrazones and Isocyanides: A Method for the Preparation of 4,5-Diaminopyrazoles
Zhang, Qian,Tang, Meng,Zhang, Siyu,Wei, Zeyang
supporting information, p. 5182 - 5186 (2020/07/04)
A facile method for the preparation of 4,5-diaminopyrazoles from N-tosylhydrazones and isocyanides was developed. The reaction was general for a wide range of substrates, and it demonstrated excellent tolerance to a variety of substituents. More important
Rhodium(III)-Catalyzed Directed C-H Dienylation of Anilides with Allenes Leads to Highly Conjugated Systems
Ghosh, Chiranjit,Nagtilak, Prajyot Jayadev,Kapur, Manmohan
supporting information, (2019/05/08)
Allenes are unique coupling partners in transition-metal-catalyzed C-H functionalization leading to a variety of products via alkenylation, allenylation, allylation, and annulation reactions. The outcome is governed by both the reactivity of the allene and the formation and stability of the organometallic intermediate. An efficient Rh(III)-catalyzed, weakly coordinating group-directed dienylation of electronically unbiased allenes is developed using an N-acyl amino acid as a ligand. Further elaboration of the dienylated products to construct polycyclic compounds is also described.
Selective C?C Coupling of Vinyl Epoxides with Diborylmethide Lithium Salts
Gava, Riccardo,Fernández, Elena
supporting information, p. 8013 - 8017 (2019/05/29)
Vinyl epoxides and styrene oxide can react with diborylmethide lithium salts through an exclusive SN2 borylmethylation/ring opening in a regio- and diastereoselective way, depending on the nature of the substrate. The ring-opening protocol prov
Diborylalkyllithium Salts Trigger Regioselective Ring Opening of Vinyl Aziridines
Salvado, Oriol,Gava, Riccardo,Fernández, Elena
supporting information, p. 9247 - 9250 (2019/11/14)
gem-Diborylalkanes treated with LiTMP produce α-diborylalkane lithium bases that perform nucleophilic attack on vinyl aziridines with controlled regioselectivity. Preferred SN2 diborylalkylation ring opening reaction on the less sterically hind
One-Pot Reaction between N-Tosylhydrazones and 2-Nitrobenzyl Bromide: Route to NH-Free C2-Arylindoles
Bzeih, Tourin,Zhang, Kena,Khalaf, Ali,Hachem, Ali,Alami, Mouad,Hamze, Abdallah
, p. 228 - 238 (2019/01/04)
A one-pot Barluenga coupling between N-tosylhydrazones and nitro-benzyl bromide, followed by deoxygenation of ortho-nitrostyrenes, and subsequent cyclization has been developed, providing a new way to synthesize various C2-arylindoles. This method exhibits a good substrate scope and functional group tolerance, and it allows an access to NH-free indoles, which can present a potential utility in medicinal chemistry applications.
One-Pot Acid-Catalyzed Ring-Opening/Cyclization/Oxidation of Aziridines with N-Tosylhydrazones: Access to 1,2,4-Triazines
Crespin, Lorène,Biancalana, Lorenzo,Morack, Tobias,Blakemore, David C.,Ley, Steven V.
supporting information, p. 1084 - 1087 (2017/03/15)
A new, three-step, telescoped reaction sequence for the regioselective conversion of N-tosyl hydrazones and aziridines to 3,6-disubstituted and 3,5,6-trisubstituted 1,2,4-triazines is described. The process involves an efficient nucleophilic ring opening of the aziridine, giving access to a wide range of aminohydrazones, isolated with excellent yields. A “one-pot” procedure, combining the ring opening with a cyclization and an oxidation step, allows the preparation of diversified triazines in good yields.
One-step synthesis of sulfonamides from N-tosylhydrazones
Tsai, Andy S.,Curto, John M.,Rocke, Benjamin N.,Dechert-Schmitt, Anne-Marie R.,Ingle, Gajendrasingh K.,Mascitti, Vincent
supporting information, p. 508 - 511 (2016/02/18)
The first described reaction between N-tosylhydrazone and SO2 is reported to provide alkyl sulfonamides in the presence of various amines. In this procedurally simple method, hydrazones of both unsaturated aldehydes and ketones proceed in moder
