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Journal articles on the topic 'N-tosylhydrazones'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Tang, Meng, and Hu Wang. "Aluminum Chloride Promoted Hantzsch Reaction of N-Tosylhydrazones." Synthesis 49, no. 21 (2017): 4893–98. http://dx.doi.org/10.1055/s-0036-1588496.

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An aluminum chloride promoted Hantzsch reaction of N-tosylhydrazones has been developed. The reaction is general for a wide range of N-tosylhydrazones, and a series of 1,4-dihydropyridines (1,4-DHPs) were prepared in moderate to excellent yields.

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2

Khanna, Avinash, Charles Maung, Kyle R. Johnson, Tom T. Luong, and David L. Van Vranken. "Carbenylative Amination with N-Tosylhydrazones." Organic Letters 14, no. 12 (2012): 3233–35. http://dx.doi.org/10.1021/ol301385g.

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3

Deng, Yu-Hua, Zhihui Shao, and Hui Wang. "An Update of N-Tosylhydrazones: Versatile Reagents for Metal-Catalyzed and Metal-Free Coupling Reactions." Synthesis 50, no. 12 (2018): 2281–306. http://dx.doi.org/10.1055/s-0036-1591993.

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N-Tosylhydrazones have had widespread application in organic synthesis for more than a half century. In most of cases, N-tosylhydrazones, as masked diazo compounds, have been generally used in a series of important carbon–carbon and carbon–heteroatom bond-forming reactions. This review provides an update on progress in diverse coupling reactions of N-tosylhydrazones since 2012. The examples selected are mainly categorized by metal-catalyzed and metal-free systems, wherein four main types of transformations including insertion, olefination, alkynylation, and cyclization are discussed for each s

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4

Phansavath, Phannarath, Virginie Ratovelomanana-Vidal, Anne Westermeyer, Quentin Llopis, and Gérard Guillamot. "Highly Regioselective Synthesis of 3,5-Substituted Pyrazoles from Bromovinyl Acetals and N-Tosylhydrazones." Synlett 31, no. 12 (2020): 1172–76. http://dx.doi.org/10.1055/s-0039-1690885.

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A regioselective synthesis of 3,5-disubstituted pyrazoles was achieved by 1,3-dipolar cycloaddition of diazo compounds, generated in situ from N-tosylhydrazones, with unactivated bromovinyl acetals, which served as alkyne surrogates. The reaction tolerated N-tosylhydrazones bearing various substituted benzylidene groups, and a range of 3,5-disubstituted pyrazoles were obtained in yields of up to 92%.

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5

Ling, Li, Jing Cao, Jianfeng Hu, and Hao Zhang. "Copper-catalyzed N-alkylation of indoles by N-tosylhydrazones." RSC Advances 7, no. 45 (2017): 27974–80. http://dx.doi.org/10.1039/c7ra03765a.

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6

Sharp, John T., and Carol E. D. Skinner. "The generation and reactions of C,N-dianions of aromatic tosylhydrazones; ortho-N-dilithiated benzophenone tosylhydrazone." Tetrahedron Letters 27, no. 7 (1986): 869–72. http://dx.doi.org/10.1016/s0040-4039(00)84123-4.

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7

Xia, Ying, and Jianbo Wang. "N-Tosylhydrazones: versatile synthons in the construction of cyclic compounds." Chemical Society Reviews 46, no. 8 (2017): 2306–62. http://dx.doi.org/10.1039/c6cs00737f.

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8

Liu, Zhenxing, Long Wang, Haocheng Tan, et al. "Synthesis of 1H-indazoles from N-tosylhydrazones and nitroaromatic compounds." Chem. Commun. 50, no. 39 (2014): 5061–63. http://dx.doi.org/10.1039/c4cc00962b.

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9

Chen, Lian-Mei, Juan Zhao, An-Jie Xia та ін. "A base-promoted cascade reaction of α,β-unsaturated N-tosylhydrazones with o-hydroxybenzyl alcohols: highly regioselective synthesis of N-sec-alkylpyrazoles". Organic & Biomolecular Chemistry 17, № 37 (2019): 8561–70. http://dx.doi.org/10.1039/c9ob01780a.

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10

Khanna, Avinash, Charles Maung, Kyle R. Johnson, Tom T. Luong, and David L. Van Vranken. "ChemInform Abstract: Carbenylative Amination with N-Tosylhydrazones." ChemInform 43, no. 41 (2012): no. http://dx.doi.org/10.1002/chin.201241027.

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11

Dai, Qiang, Yan Jiang, Songjin Guo, Jin-Tao Yu та Jiang Cheng. "3-Aza π-allyl palladium derived from imino migration in palladium-carbene: MCRs toward multiple substituted indole skeleton". Chemical Communications 51, № 79 (2015): 14781–84. http://dx.doi.org/10.1039/c5cc05984d.

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12

Lin, Yuqing, Puying Luo, Qiang Zheng, Yumei Liu, Xiaoyan Sang, and Qiuping Ding. "Efficient construction of C–S and C–N bonds via metal-free reductive coupling of N-tosylhydrazones with benzo[d]thiazole-2-thiol." RSC Adv. 4, no. 32 (2014): 16855–63. http://dx.doi.org/10.1039/c4ra00590b.

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13

Lingayya, Rajaka, Mari Vellakkaran, Kommu Nagaiah, Prabhakar Rao Tadikamalla, and Jagadeesh Babu Nanubolu. "Palladium(ii)-catalyzed direct O-alkenylation of 2-arylquinazolinones with N-tosylhydrazones: an efficient route to O-alkenylquinazolines." Chemical Communications 53, no. 10 (2017): 1672–75. http://dx.doi.org/10.1039/c6cc09445g.

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14

Hong, Ji Young, Ue Ryung Seo, and Young Keun Chung. "Synthesis of carbamates from amines and N-tosylhydrazones under atmospheric pressure of carbon dioxide without an external base." Organic Chemistry Frontiers 3, no. 6 (2016): 764–67. http://dx.doi.org/10.1039/c6qo00111d.

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15

Chen, Pengquan, Chuanle Zhu, Rui Zhu, Zhiming Lin, Wanqing Wu, and Huanfeng Jiang. "Synthesis of 3-azabicyclo[3.1.0]hexane derivatives via palladium-catalyzed cyclopropanation of maleimides with N-tosylhydrazones: practical and facile access to CP-866,087." Organic & Biomolecular Chemistry 15, no. 5 (2017): 1228–35. http://dx.doi.org/10.1039/c6ob02137a.

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16

Paraja, Miguel, and Carlos Valdés. "Pd-catalyzed cascade reactions between o-iodo-N-alkenylanilines and tosylhydrazones: novel approaches to the synthesis of polysubstituted indoles and 1,4-dihydroquinolines." Chemical Communications 52, no. 37 (2016): 6312–15. http://dx.doi.org/10.1039/c6cc01880g.

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17

Tsai, Andy S., John M. Curto, Benjamin N. Rocke, Anne-Marie R. Dechert-Schmitt, Gajendrasingh K. Ingle, and Vincent Mascitti. "One-Step Synthesis of Sulfonamides from N-Tosylhydrazones." Organic Letters 18, no. 3 (2016): 508–11. http://dx.doi.org/10.1021/acs.orglett.5b03545.

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18

Zhou, Fengtao, Ke Ding, and Qian Cai. "Palladium-Catalyzed Amidation of N-Tosylhydrazones with Isocyanides." Chemistry - A European Journal 17, no. 44 (2011): 12268–71. http://dx.doi.org/10.1002/chem.201102459.

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19

Wu, Xufeng, Lingyu Li, Wenlong Jiang, Lihong Zhou, and Qingle Zeng. "Copper-catalyzed C-N coupling reaction of tosylhydrazones." Applied Organometallic Chemistry 32, no. 10 (2018): e4483. http://dx.doi.org/10.1002/aoc.4483.

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20

Wu, Guojiao, Yifan Deng, Haiqing Luo та ін. "Transition-metal-free cascade reaction of α-halo-N-tosylhydrazones, indoles and arylboronic acids". Chemical Communications 52, № 30 (2016): 5266–68. http://dx.doi.org/10.1039/c6cc01750a.

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21

Shen, Xu, Ningning Gu, Ping Liu, et al. "A simple and efficient synthesis of 9-arylfluorenes via metal-free reductive coupling of arylboronic acids and N-tosylhydrazones in situ." RSC Advances 5, no. 78 (2015): 63726–31. http://dx.doi.org/10.1039/c5ra12099c.

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22

Guru, Murali Mohan, Sriman De, Sayan Dutta, Debasis Koley, and Biplab Maji. "B(C6F5)3-catalyzed dehydrogenative cyclization of N-tosylhydrazones and anilines via a Lewis adduct: a combined experimental and computational investigation." Chemical Science 10, no. 34 (2019): 7964–74. http://dx.doi.org/10.1039/c9sc02492a.

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23

Huang, Yubing, Xianwei Li, Xu Wang, et al. "Copper-catalyzed cyanothiolation to incorporate a sulfur-substituted quaternary carbon center." Chemical Science 8, no. 10 (2017): 7047–51. http://dx.doi.org/10.1039/c7sc02867a.

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24

Luo, Haiqing, Guojiao Wu, Shuai Xu, et al. "Palladium-catalyzed cross-coupling of aryl fluorides with N-tosylhydrazones via C–F bond activation." Chemical Communications 51, no. 68 (2015): 13321–23. http://dx.doi.org/10.1039/c5cc05035a.

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A palladium-catalyzed cross-coupling reaction of electron-deficient aryl fluorides with aryl N-tosylhydrazones, which involves C–F bond activation and migratory insertion of palladium carbene, has been developed.

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25

Zhou, Qi, Yunpeng Gao, Yiyang Xiao, et al. "Palladium-catalyzed carbene coupling of N-tosylhydrazones and arylbromides to synthesize cross-conjugated polymers." Polymer Chemistry 10, no. 5 (2019): 569–73. http://dx.doi.org/10.1039/c8py01529e.

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Palladium-catalyzed cross-coupling reactions of N-tosylhydrazones and arylbromides have been applied for the first time in the synthesis of cross-conjugated polymers, namely poly(arylene-1,1-vinylidene)s (iso-PAVs).

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26

Reddy Lonka, Madhava, Jinquan Zhang, Thirupathi Gogula, and Hongbin Zou. "Copper(i)-catalyzed benzylation of triazolopyridine through direct C–H functionalization." Organic & Biomolecular Chemistry 17, no. 32 (2019): 7455–60. http://dx.doi.org/10.1039/c9ob01433k.

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27

Barroso, Raquel, María-Paz Cabal, Azucena Jiménez, and Carlos Valdés. "Cascade and multicomponent synthesis of structurally diverse 2-(pyrazol-3-yl)pyridines and polysubstituted pyrazoles." Organic & Biomolecular Chemistry 18, no. 8 (2020): 1629–36. http://dx.doi.org/10.1039/c9ob02691f.

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A wide diversity of polyheterocyclic systems including polysubstituted pyrazoles and pyridopyrazole polydentate ligands are readily assembled through cascade multicomponent processes from terminal alkynes and N-tosylhydrazones.

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28

Ma, Liang, Feng Jin, Xionglve Cheng, et al. "[2 + 2 + 1] Cycloaddition of N-tosylhydrazones, tert-butyl nitrite and alkenes: a general and practical access to isoxazolines." Chemical Science 12, no. 28 (2021): 9823–30. http://dx.doi.org/10.1039/d1sc02352g.

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29

Valdés, Carlos, Raquel Barroso, and María Cabal. "Pd-catalyzed Auto-Tandem Cascades Based on N-Sulfonylhydrazones: Hetero- and Carbocyclization Processes." Synthesis 28, no. 19 (2017): 4434–47. http://dx.doi.org/10.1055/s-0036-1588535.

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The Pd-catalyzed cross-coupling between N-tosylhydrazones and organic halides is a powerful method for the creation of C–C bonds. This transformation has been included recently in cascade processes in which the same catalyst promotes various independent catalytic steps, a process known as auto-tandem catalysis. This strategy proves to be very useful for the construction of relatively complex carbo- and heterocyclic structures, as well as for the generation of molecular diversity. This short review will cover the different Pd-catalyzed auto-tandem reactions involving N-tosylhydrazones organize

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30

Valdés, Carlos, Miguel Paraja, and Manuel Plaza. "Transition-Metal-Free Reactions Between Boronic Acids and N-Sulfonylhydrazones or Diazo Compounds: Reductive Coupling Processes and Beyond." Synlett 28, no. 18 (2017): 2373–89. http://dx.doi.org/10.1055/s-0036-1590868.

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The metal-free reaction between diazo compounds and boronic acids has been established in recent years as a powerful C(sp3)–C bond-forming reaction. This account covers the recent advances in this area. First, the various synthetic applications of reactions with N-sulfonylhydrazones as a convenient source of diazo compounds is discussed. These transformations can be regarded as reductive couplings of carbonyl compounds. Also covered is the incorporation of other mild sources of diazo compounds in these reactions: diazotization of amines and oxidation of hydrazones. Finally, the development of

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31

Yu, Wei, Shichao Yang, Pei-Long Wang, Pinhua Li та Hongji Li. "BF3·OEt2-mediated cyclization of β,γ-unsaturated oximes and hydrazones with N-(arylthio/arylseleno)succinimides: an efficient approach to synthesize isoxazoles or dihydropyrazoles". Organic & Biomolecular Chemistry 18, № 36 (2020): 7165–73. http://dx.doi.org/10.1039/d0ob01388a.

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An efficient BF<sub>3</sub>·OEt<sub>2</sub>-mediated cyclization of β,γ-unsaturated oximes and tosylhydrazones with N-(arylthio/arylseleno)succinimides has been established for building isoxazoles and dihydropyrazoles.

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32

Ragupathi, Ayyakkannu, Arunachalam Sagadevan, Vaibhav Pramod Charpe, Chun-Cheng Lin, Jih-Ru Hwu, and Kuo Chu Hwang. "Visible-light-driven copper-catalyzed aerobic oxidative cascade cyclization of N-tosylhydrazones and terminal alkynes: regioselective synthesis of 3-arylcoumarins." Chemical Communications 55, no. 35 (2019): 5151–54. http://dx.doi.org/10.1039/c9cc01801h.

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An intuitive visible-light-driven copper-catalyzed process can accomplish regioselective functionalized 3-arylcoumarins via oxidative annulation of simple N-tosylhydrazones with terminal alkynes under O<sub>2</sub> (1 atm.) at room temperature.

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33

Kong, Yuanfang, Wen Zhang, Meng Tang, and Haiming Wang. "N-Alkylation of tosylhydrazones in the presence of triphenylphosphine." Tetrahedron 69, no. 35 (2013): 7487–91. http://dx.doi.org/10.1016/j.tet.2013.05.131.

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34

Reddy, Ch Raji, and E. Jithender. "Acid-catalyzed N-alkylation of tosylhydrazones using benzylic alcohols." Tetrahedron Letters 50, no. 40 (2009): 5633–35. http://dx.doi.org/10.1016/j.tetlet.2009.07.093.

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35

Zhang, Qian, and Meng Tang. "Regioselective Synthesis of Highly Functionalized Pyrazoles from N-Tosylhydrazones." Organic Letters 21, no. 6 (2019): 1917–20. http://dx.doi.org/10.1021/acs.orglett.9b00561.

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36

Arunprasath, Dhanarajan, Balasubramanian Devi Bala, and Govindasamy Sekar. "Luxury of N ‐Tosylhydrazones in Transition‐Metal‐Free Transformations." Advanced Synthesis & Catalysis 361, no. 6 (2018): 1172–207. http://dx.doi.org/10.1002/adsc.201801031.

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37

Theerthagiri, P., and A. Lalitha. "Iodine-catalyzed N-alkylation of tosylhydrazones with benzylic alcohols." Journal of the Iranian Chemical Society 10, no. 4 (2012): 717–24. http://dx.doi.org/10.1007/s13738-012-0205-1.

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38

Wei, Siping, Shuangxun Li, Changyou Chen, et al. "Access to Fluorescent Azines from N-Heterocyclic Carbene Precursors and N -Tosylhydrazones." Advanced Synthesis & Catalysis 359, no. 11 (2017): 1825–30. http://dx.doi.org/10.1002/adsc.201700241.

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39

Xiao, Qing, Lin Ling, Fei Ye, et al. "Copper-Catalyzed Direct Ortho-Alkylation of N-Iminopyridinium Ylides with N-Tosylhydrazones." Journal of Organic Chemistry 78, no. 8 (2013): 3879–85. http://dx.doi.org/10.1021/jo4002883.

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40

Fu, Xinliang, Haotao Li, Demin Ren, and Xiaofang Li. "Synthesis of Chromeno[3,4-c]Pyrazole from N-Tosylhydrazones and 3-Nitro-2-Phenyl-2H-Chromene." Journal of Chemical Research 41, no. 12 (2017): 709–11. http://dx.doi.org/10.3184/174751917x15125690124255.

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The intermolecular 1,3-dipolar cycloaddition of N-tosylhydrazones and 3-nitro-2-phenyl-2 H-chromene afforded 1-aryl-4-phenyl-2,4-dihydro-chromeno[3,4- c]pyrazoles in moderate to good yields. The structures of all the products were characterised by NMR, IR, HRMS and X-ray crystallographic analysis.

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41

Pilania, Meenakshi, Arun Velladurai, Mukund P. Tantak, and Dalip Kumar. "Cu-Catalyzed Expeditious Synthesis of N-Benzylaminoheter-ocycles Using N-Tosylhydrazones and Aminoheteroarenes." ChemistrySelect 1, no. 20 (2016): 6368–73. http://dx.doi.org/10.1002/slct.201601734.

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42

Ishitobi, Kota, Kei Muto, and Junichiro Yamaguchi. "Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones." ACS Catalysis 9, no. 12 (2019): 11685–90. http://dx.doi.org/10.1021/acscatal.9b04212.

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43

Zhang, Zhikun, Weizhi Yu, Qi Zhou, Tianjiao Li, Yan Zhang, and Jianbo Wang. "Rh(I)-Catalyzed Reaction of Trifluoromethylketone N -Tosylhydrazones and Arylboronates." Chinese Journal of Chemistry 34, no. 5 (2016): 473–76. http://dx.doi.org/10.1002/cjoc.201500889.

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44

Zhou, Fengtao, Ke Ding, and Qian Cai. "ChemInform Abstract: Palladium-Catalyzed Amidation of N-Tosylhydrazones with Isocyanides." ChemInform 43, no. 11 (2012): no. http://dx.doi.org/10.1002/chin.201211061.

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45

Sun, Zhenze, Jing He, Weiwei Li, et al. "Pd‐Catalyzed Regioselective Olefination of N ‐Tosylhydrazones with Benzyl Bromides." ChemistrySelect 5, no. 25 (2020): 7396–99. http://dx.doi.org/10.1002/slct.202002010.

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46

Radolko, Jan, Peter Ehlers, and Peter Langer. "Recent Advances in Transition‐Metal‐Catalyzed Reactions of N‐Tosylhydrazones." Advanced Synthesis & Catalysis 363, no. 15 (2021): 3616–54. http://dx.doi.org/10.1002/adsc.202100332.

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47

Campos, Vinicius R., Ana T. P. C. Gomes, Anna C. Cunha, Maria da Graça P. M. S. Neves, Vitor F. Ferreira та José A. S. Cavaleiro. "Efficient access to β-vinylporphyrin derivatives via palladium cross coupling of β-bromoporphyrins with N-tosylhydrazones". Beilstein Journal of Organic Chemistry 13 (30 січня 2017): 195–202. http://dx.doi.org/10.3762/bjoc.13.22.

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This work describes a new approach to obtain new β-vinylporphyrin derivatives through palladium-catalyzed cross-coupling reaction of 2-bromo-5,10,15,20-tetraphenylporphyrinatozinc(II) with N-tosylhydrazones. This is the first report of the use of such synthetic methodology in porphyrin chemistry allowing the synthesis of new derivatives, containing β-arylvinyl substituents.

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48

Blay, Gonzalo, Elisabeth Benach, Isabel Fernández, Sales Galletero, José R. Pedro, and Rafael Ruiz. "Catalytic Aerobic Oxidative Cleavage of Oximes, Tosylhydrazones and N,N-Dimethylhydrazones to Carbonyl Compounds." Synthesis 2000, no. 03 (2000): 403–6. http://dx.doi.org/10.1055/s-2000-6347.

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49

Dehmlow, Eckehard Volker, and Stephanie Düttmann. "Notes on a Recent Paper About the Cleavage of N,N-Dimethylhydrazones and Tosylhydrazones." Synthetic Communications 30, no. 12 (2000): 2239–43. http://dx.doi.org/10.1080/00397910008087403.

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50

Xiao, Qing, Lin Ling, Fei Ye, et al. "ChemInform Abstract: Copper-Catalyzed Direct ortho-Alkylation of N-Iminopyridinium Ylides with N-Tosylhydrazones." ChemInform 44, no. 34 (2013): no. http://dx.doi.org/10.1002/chin.201334146.

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