75230-51-2Relevant academic research and scientific papers
One-pot synthesis of sulfonylhydrazones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water
Luo, Mengqiang,Wang, Hai,Ren, Xiaorong,Lu, Ruijuan,Qi, Chenze,Zhang, Yaohong,Shen, Runpu
, p. 2713 - 2722 (2021/03/19)
A facile and eco-friendly protocol for the synthesis of sulfonylhydrazones from sulfonyl chlorides, hydrazine hydrate and vinyl azides was developed. The unique advantage of this approach is that desired products can be obtained efficiently in water, which meets the requirements of green chemistry and provides good perspectives for the sustainable production of new drug candidate. Also, this reaction proceeded in moderate to good yields with a wide tolerance of functional groups.
Pd-Catalyzed Coupling of Thioamides with N-Tosylhydrazones/Trapping by Esters Cascade Reaction
Cai, Zhongliang,Yao, Zhi,Jiang, Liqin
supporting information, p. 311 - 316 (2021/01/26)
N,N-Disubstituted thioamides coupled with N-tosylhydrazones under Pd(TFA)2/tBuXPhos catalyst and NaOtBu, and the intermediates from palladium carbene migratory insertion containing β-hydrogen were trapped by intramolecular esters activated by BF3·Et2O ins
Copper(I)/Bpy-Catalyzed C-2-H Benzylation of Quinazolin-4(3H)-ones with N-Tosylhydrazones
Li, Fei,Gu, Xiao-Juan,Zeng, Chang-E.,Li, Xia,Liu, Bo,Huang, Guo-Li
, p. 2923 - 2928 (2020/05/16)
A general and efficient copper-catalyzed C–H benzylation reaction of quinazolin-4(3H)-ones with N-tosylhydrazones is reported. The formation of new C(sp3)–C(sp2) bonds through cross-coupling occurs at the electron-poor C-2 position of quinazolin-4(3H)-one and represents an exceedingly practical method to afford 2-benzylated quinazolin-4(3H)-ones in moderate to good yields under mild reaction conditions. A possible reaction mechanism for this transformation was proposed. This catalytic transformation has the potential to be an important synthetic application for the late-stage functionalization of advanced synthetic intermediates.
Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay
Wang, Shun,Cheng, Bei-Yi,Sr?en, Matea,K?nig, Burkhard
supporting information, p. 7524 - 7531 (2020/08/05)
The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.
I2-Promoted [4 + 2] cycloaddition of: In situ generated azoalkenes with enaminones: Facile and efficient synthesis of 1,4-dihydropyridazines and pyridazines
Baell, Jonathan B.,Feng, Jiajun,He, Tiantong,Huang, Fei,Xie, Yuxing,Yu, Yang
supporting information, p. 9483 - 9493 (2020/12/15)
A facile and efficient strategy for the synthesis of 1,4-dihydropyridazines and pyridazines through I2-promoted [4 + 2] cycloaddition of in situ generated azoalkenes with enaminones has been developed. The switch in selectivity is attributed to the judici
Sulfonylhydrazone derivative, and preparation method and application thereof
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Paragraph 0036; 0037; 0053-0055; 0056; 0057, (2020/01/03)
The invention discloses a sulfonylhydrazone derivative, and a preparation method and application thereof. The preparation method comprises the following step of taking olefin azide and sulfonyl hydrazine as starting materials to carry out a reaction, wher
Copper(i)-catalyzed benzylation of triazolopyridine through direct C-H functionalization
Reddy Lonka, Madhava,Zhang, Jinquan,Gogula, Thirupathi,Zou, Hongbin
, p. 7455 - 7460 (2019/08/20)
A general and efficient copper-catalyzed benzylation reaction of triazolopyridine with N-tosylhydrazones was developed. This reaction forms a C(sp2)-C(sp3) bond through cross-coupling, and represents an exceedingly practical method t
Lewis Acid Catalyzed [4 + 2] Cycloaddition of N-Tosylhydrazones with ortho-Quinone Methides
Wang, Chun-Ying,Han, Jia-Bin,Wang, Long,Tang, Xiang-Ying
, p. 14258 - 14269 (2019/11/11)
A formal [4 + 2] cycloaddition of N-tosylhydrazones with ortho-quinone methides was developed, affording the facile synthesis of diverse 1,3-oxazine derivatives under mild conditions. In this transformation, N-tosylhydrazones are used as a 1,2-dipole synt
Synthesis of Multi-substituted Dihydropyrazoles by Copper-Mediated [4+1] Cycloaddition Reaction of N-Sulfonylhydrazones and Sulfoxonium Ylides
Hu, Sipei,Du, Shiying,Yang, Zuguang,Ni, Lingfang,Chen, Zhengkai
supporting information, p. 3124 - 3136 (2019/05/01)
A general and expeditious approach for the copper mediated synthesis of multi-functionalized dihydropyrazoles from N-sulfonylhydrazones and sulfoxonium ylides has been achieved under aerobic oxidative conditions. The formal [4+1] cycloaddition reaction ex
Asymmetric Copper-Catalyzed C(sp)-H Bond Insertion of Carbenoids Derived from N-Tosylhydrazones
Osako, Takao,Nagaosa, Makoto,Hamasaka, Go,Uozumi, Yasuhiro
supporting information, p. 2251 - 2256 (2018/10/20)
A chiral copper(I)-phosphoramidite complex efficiently catalyzed the asymmetric insertion of the carbenoids derived from N-tosyl hydrazones into alkyne C-H bonds to give the corresponding chiral alkynylated products in up to 77% yield and with up to 74% e
