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Journal articles on the topic 'TosMIC'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

Bounar, Haniya, Zhenhua Liu, Lin Zhang, et al. "Silver-catalyzed cascade reaction of tosylmethyl isocyanide (TosMIC) with propargylic alcohols to (E)-vinyl sulfones: dual roles of TosMIC." Organic & Biomolecular Chemistry 13, no. 32 (2015): 8723–28. http://dx.doi.org/10.1039/c5ob01129a.

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An silver-catalyzed cascade reaction of tosylmethyl isocyanide (TosMIC) with propargylic alcohols for the synthesis of (E)-vinyl sulfones has been developed where TosMIC plays a dual role as both the reactant in the allenylation of propargylic alcohols and the sulfonyl source.

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2

Chen, Wenteng, Jiaan Shao, Zhi Li, Marc A. Giulianotti, and Yongping Yu. "Synthesis of 2,3,4-trisubstituted pyrroles via a facile reaction of vinyl azides and tosylmethyl isocyanide." Canadian Journal of Chemistry 90, no. 2 (2012): 214–21. http://dx.doi.org/10.1139/v11-150.

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A facile synthesis of polysubstituted pyrroles from tosylmethyl isocyanide (TOSMIC) and readily synthesized vinyl azides was developed. The reaction proceeded under mild conditions in the presence of base. 2-Tosyl-substituted pyrroles were obtained in moderate to good isolated yields. Additionally, a base-initiated one-pot pyrrole synthesis also was developed using carboxaldehydes, ethyl 2-azidoacetate, and TOSMIC.

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3

Ramana Reddy, V. V. "p-Toluenesulfonylmethyl Isocyanide (TosMIC)." Synlett, no. 2 (2005): 363–64. http://dx.doi.org/10.1055/s-2004-837237.

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4

Gotsko, Maxim D., Ivan V. Saliy, Igor A. Ushakov, Lyubov N. Sobenina, and Boris A. Trofimov. "Functionalized 2,3′-Bipyrroles and Pyrrolo[1,2-c]imidazoles from Acylethynylpyrroles and Tosylmethylisocyanide." Molecules 29, no. 4 (2024): 885. http://dx.doi.org/10.3390/molecules29040885.

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An efficient method for the synthesis of pharmaceutically prospective but still rare functionalized 2,3′-bipyrroles (in up to 80% yield) by the cycloaddition of easily available acylethynylpyrroles with tosylmethylisocyanide (TosMIC) has been developed. The reaction proceeds under reflux (1 h) in the KOH/THF system. In the t-BuONa/THF system, TosMIC acts in two directions: along with 2,3′-bipyrroles, the unexpected formation of pyrrolo[1,2-c]imidazoles is also observed (products ratio~1:1).

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5

Mathiyazhagan, Arun Divakar, and Gopinathan Anilkumar. "Recent advances and applications of p-toluenesulfonylmethyl isocyanide (TosMIC)." Organic & Biomolecular Chemistry 17, no. 28 (2019): 6735–47. http://dx.doi.org/10.1039/c9ob00847k.

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6

Qu, Chuanhua, Run Huang, Yong Li, Tong Liu, Yuan Chen, and Guiting Song. "Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group." Beilstein Journal of Organic Chemistry 17 (December 2, 2021): 2822–31. http://dx.doi.org/10.3762/bjoc.17.193.

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Chemoselective sulfonylation and isonitrilation reactions for the divergent synthesis of valuable diarylmethyl sulfones and isonitrile diarylmethanes starting from easy-to-synthesize para-quinone methides (p-QMs) and commercially abundant p-toluenesulfonylmethyl isocyanide (TosMIC) by using respectively zinc iodide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as catalysts were developed. The distinguishing feature of this method is that TosMIC plays a dual role from the same substrates in the reaction: as a sulfonyl source or as an isonitrile source. The synthetic utility of this protocol was

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7

Phanindrudu, Mandalaparthi, Dipak Kumar Tiwari, B. Sridhar, Pravin R. Likhar, and Dharmendra Kumar Tiwari. "Magnetically separable nano-copper catalyzed unprecedented stereoselective synthesis of E-vinyl sulfones from tosylmethyl isocyanide and alkynes: TosMIC as a source of the sulfonyl group." Organic Chemistry Frontiers 3, no. 7 (2016): 795–98. http://dx.doi.org/10.1039/c6qo00063k.

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8

Fan, Cai-Ling, Lin-Bao Zhang, Jia Liu, Xin-Qi Hao, Jun-Long Niu, and Mao-Ping Song. "Copper-mediated direct sulfonylation of C(sp2)–H bonds employing TosMIC as a sulfonyl source." Organic Chemistry Frontiers 6, no. 13 (2019): 2215–19. http://dx.doi.org/10.1039/c9qo00391f.

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9

Kaur, Tanpreet, Preeti Wadhwa, and Anuj Sharma. "Arylsulfonylmethyl isocyanides: a novel paradigm in organic synthesis." RSC Advances 5, no. 65 (2015): 52769–87. http://dx.doi.org/10.1039/c5ra07876h.

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p-Tosylmethyl isocyanide (TosMIC), an α-acidic isocyanide has emerged as a privileged reagent to access biologically relevant fused heterocycles and some natural products like (−)-ushikulide A, variolin B, porphobilinogen and mansouramycin B.

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10

Kulkarni, Bheemashankar A., and A. Ganesan. "Solution-phase parallel oxazole synthesis with TosMIC." Tetrahedron Letters 40, no. 30 (1999): 5637–38. http://dx.doi.org/10.1016/s0040-4039(99)01050-3.

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11

Breitenbach, Jörg, and Fritz Vögtle. "Macrocyclizations with TosMIC - Yielding [3 n ]Metacyclophanes." Synthesis 1992, no. 1/2 (1992): 41–43. http://dx.doi.org/10.1055/s-1992-34171.

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12

Gutiérrez, Sara, David Sucunza та Juan J. Vaquero. "γ-Carboline Synthesis by Heterocyclization of TosMIC Derivatives". Journal of Organic Chemistry 83, № 12 (2018): 6623–32. http://dx.doi.org/10.1021/acs.joc.8b00906.

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13

Kumar, Kapil. "TosMIC: A Powerful Synthon for Cyclization and Sulfonylation." ChemistrySelect 5, no. 33 (2020): 10298–328. http://dx.doi.org/10.1002/slct.202001344.

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14

BREITENBACH, J., and F. VOEGTLE. "ChemInform Abstract: Macrocyclizations with TosMIC - Yielding (3 )Metacyclophanes." ChemInform 23, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.199230077.

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15

Lujan-Montelongo, J. Armando, Angel Ojeda Estevez, and Fraser F. Fleming. "Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs." European Journal of Organic Chemistry 2015, no. 7 (2015): 1602–5. http://dx.doi.org/10.1002/ejoc.201403615.

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16

Liu, Jianquan, Zhenhua Liu, Peiqiu Liao, and Xihe Bi. "Modular Synthesis of Sulfonyl Benzoheteroles by Silver-Catalyzed Heteroaromatization of Propargylic Alcohols with p-Toluenesulfonylmethyl Isocyanide (TosMIC): Dual Roles of TosMIC." Organic Letters 16, no. 23 (2014): 6204–7. http://dx.doi.org/10.1021/ol5031316.

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17

Bounar, Haniya, Zhenhua Liu, Lin Zhang, et al. "ChemInform Abstract: Silver-Catalyzed Cascade Reaction of Tosylmethyl Isocyanide (TosMIC) with Propargylic Alcohols to (E)-Vinyl Sulfones: Dual Roles of TosMIC." ChemInform 46, no. 50 (2015): no. http://dx.doi.org/10.1002/chin.201550088.

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18

Prapurna, Y., Naresh Pogaku, and Palakodety Krishna. "An Efficient Direct Access to Carbamates from Alcohols and TosMIC Mediated by Iodine in DMSO." Synlett 29, no. 15 (2018): 2039–42. http://dx.doi.org/10.1055/s-0037-1610229.

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A new approach for the synthesis of carbamates from alcohols and TosMIC promoted by iodine/DMSO system is reported. This method offers a one-step, direct and practical strategy for the rapid construction of carbamates under mild conditions. The reaction proceeds via sequential oxidation of isocyanide to isocyanate and nucleophilic addition of alcohols to isocyanate to afford the carbamates in high yields.

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19

Dhanalakshmi, Pandi, and Sivakumar Shanmugam. "Convenient one-pot multicomponent strategy for the synthesis of 6-pyrrolylpyrimidines." RSC Adv. 4, no. 56 (2014): 29493–501. http://dx.doi.org/10.1039/c4ra02891k.

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An easy method to construct diheteroaryls from α-aroylidineketene dithioacetals 2 in a multicomponent fashion. The reaction proceeds with high chemo/regioselectivity to give 4-alkoxy-6-(4-aryl-1H-pyrrol-3-yl)pyrimidin-2-amines in high yields by reacting 2 with p-tolylsulfonyl)methyl isocyanide 3 (TosMIC), guanidine nitrate 5 and alcohol in the presence of NaH/THF via cycloaddition.

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20

Kulkarni, Bheemashankar A., and A. Ganesan. "ChemInform Abstract: Solution-Phase Parallel Oxazole Synthesis with TosMIC." ChemInform 30, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199944133.

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21

DI SANTO, R., S. MASSA, and M. ARTICO. "ChemInform Abstract: Synthesis of Biologically Active Azoles via TosMIC." ChemInform 24, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199336284.

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22

Liu, Jianquan, Zhenhua Liu, Peiqiu Liao, and Xihe Bi. "ChemInform Abstract: Modular Synthesis of Sulfonyl Benzoheteroles by Silver-Catalyzed Heteroaromatization of Propargylic Alcohols with p-Toluenesulfonylmethyl Isocyanide (TosMIC): Dual Roles of TosMIC." ChemInform 46, no. 18 (2015): no. http://dx.doi.org/10.1002/chin.201518098.

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23

Santo, Roberto Di, Roberta Costi, Carlo Galeffi, and Michela Forte. "REGIOSELECTIVITY OF THE METHYL-TOSMIC REACTION WITH SUBSTITUTED ETHYL CINNAMATES." Organic Preparations and Procedures International 37, no. 2 (2005): 178–83. http://dx.doi.org/10.1080/00304940509354884.

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24

Radha Krishna, Palakodety, and Krishnarao Lopinti. "Diastereoselective Passerini Reaction of Chiral 2,3-Epoxy Aldehydes with TosMIC." Synlett 2007, no. 1 (2007): 0083–86. http://dx.doi.org/10.1055/s-2006-958441.

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25

Radha Krishna, Palakodety, E. Raja Sekhar, and Y. Lakshmi Prapurna. "InCl3 catalyzed C–C coupling of aryl alcohols and TosMIC." Tetrahedron Letters 48, no. 51 (2007): 9048–50. http://dx.doi.org/10.1016/j.tetlet.2007.09.164.

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26

Sisko, Joseph, Mark Mellinger, Peter W. Sheldrake, and Neil H. Baine. "An efficient method for the synthesis of substituted TosMIC precursors." Tetrahedron Letters 37, no. 45 (1996): 8113–16. http://dx.doi.org/10.1016/0040-4039(96)01886-2.

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27

Lujan-Montelongo, J. Armando, Angel Ojeda Estevez, and Fraser F. Fleming. "ChemInform Abstract: Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogues." ChemInform 46, no. 27 (2015): no. http://dx.doi.org/10.1002/chin.201527112.

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28

Franchino, Allegra, Jack Chapman, Ignacio Funes-Ardoiz, Robert S. Paton, and Darren J. Dixon. "Catalytic Enantio- and Diastereoselective Mannich Addition of TosMIC to Ketimines." Chemistry - A European Journal 24, no. 67 (2018): 17660–64. http://dx.doi.org/10.1002/chem.201804099.

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29

Kotha, Sambasivarao, and Subba Rao Cheekatla. "Synthesis of Bisoxazole and Bromo-substituted Aryloxazoles." Molbank 2022, no. 3 (2022): M1440. http://dx.doi.org/10.3390/m1440.

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Herein, we report a bisoxazole derivative as well as a bromo-substituted oxazole derivatives via a simple approach. The synthesis begins with an inexpensive and readily available starting material, such as 2,5-dimethoxybenzaldehyde, hydroquinone, and p-toluenesulfonylmethyl isocyanide (TosMIC). This approach relies on the Van Leusen oxazole method and electrophilic aromatic bromination. The structures of bisoxazole and bromosubstituted aryloxazoles were fully supported by spectroscopic methods (IR, NMR, and HRMS) and further established using single crystal X-ray diffraction studies.

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30

Trilleras, Jorge, Jairo Quiroga, and Angelina Hormaza. "Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method." Molbank 2022, no. 1 (2022): M1341. http://dx.doi.org/10.3390/m1341.

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The synthesis and structural diversification of N-heterocycles systems have attracted much attention because of their potential applications. Three 6-aryl-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde 4 derivatives, in reaction with acetophenones 5, via conventional Claisen–Schmidt condensation reactions, generated the respective enones. The enones were used as electron-deficient olefins in a “formal” [2+3] cycloaddition reaction using p-tosylmethyl isocyanide—TosMIC 7. This protocol allows access to 3-(substituted aroyl)-4-heteroaryl pyrrole derivatives by the Van Leusen method.

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31

Sisko, Joseph, and Mark Mellinger. "Development of a general process for the synthesis of highly substituted imidazoles." Pure and Applied Chemistry 74, no. 8 (2002): 1349–57. http://dx.doi.org/10.1351/pac200274081349.

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Several highly substituted imidazoles have been under investigation at GlaxoSmithKline as potential therapies for the treatment of rheumatoid arthritis and have spawned the need for a general synthetic method for their preparation on a multikilogram scale. We describe herein the optimization of a general method for the preparation of aryl-substituted TosMIC reagents and the ease with which they undergo [3+2] cycloadditions with a host of imines, prepared in situ, to generate densely functionalized imidazoles with various substitution patterns in a completely regioselective manner.

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32

R. Katritzky, Alan, Dai Cheng, and Richard P. Musgrave. "Syntheses of Imidazoles and Pyrroles: BetMIC and TosMIC as Complementary Reagents." HETEROCYCLES 44, no. 1 (1997): 67. http://dx.doi.org/10.3987/com-95-s5.

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33

González-Zamora, Eduardo, Ma García-González, Rosa Santillan, and Norberto Farfán. "Synthesis of 2-Imino-3-aminobenzofurans via Multicomponent Reactions from TosMIC." Synlett 2011, no. 03 (2011): 308–10. http://dx.doi.org/10.1055/s-0030-1259325.

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34

Keeri, Abdul Raheem, Andrea Gualandi, Andrea Mazzanti, Janusz Lewinski, and Pier Giorgio Cozzi. "Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones." Chemistry - A European Journal 21, no. 52 (2015): 18949–52. http://dx.doi.org/10.1002/chem.201504362.

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35

Lamberth, Clemens. "p-Tolysulfonylmethyl Isocyanide (TosMIC) - a versatile formaldehyde equivalent with reversed polarity." Journal f�r Praktische Chemie/Chemiker-Zeitung 340, no. 5 (1998): 483–85. http://dx.doi.org/10.1002/prac.19983400514.

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36

DI SANTO, R., R. COSTI, S. MASSA, and M. ARTICO. "ChemInform Abstract: Simple Synthetic Approach to Arylacetic NSAIAs via TosMIC Procedure." ChemInform 26, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199527059.

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37

Li, Yigao, Xu-Yan Wang, Xiaohuang Ren, et al. "Iron-Mediated Selective Sulfonylmethylation of Aniline Derivatives with p-Toluenesulfonylmethyl Isocyanide (TosMIC)." Journal of Organic Chemistry 86, no. 10 (2021): 7179–88. http://dx.doi.org/10.1021/acs.joc.1c00500.

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38

Terzidis, Michael A., Julia Stephanidou-Stephanatou, and Constantinos A. Tsoleridis. "Chromone-3-carboxaldehydes in Passerini Reactions Using TosMIC as the Isonitrile Component." Open Organic Chemistry Journal 2, no. 1 (2008): 88–91. http://dx.doi.org/10.2174/1874095200801020088.

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39

Fangli Qiu, Jianwei Wu, Yaohong Zhang, et al. "A Novel Synthesis of Multisubstituted Pyrroles via Trisubstituted Olefins and TosMIC Derivatives." Letters in Organic Chemistry 9, no. 4 (2012): 305–8. http://dx.doi.org/10.2174/157017812800233778.

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40

Aderohunmu, Damilola V., Taiwo T. Odutola, Olayinka O. Ajani, and Ezekiel F. Adebiyi. "TOSMIC REAGENT: AN EXCELLENT PRECURSOR IN THE SYNTHESIS OF BIOLOGICALLY ACTIVE HETEROCYCLES." Rasayan Journal of Chemistry 12, no. 04 (2019): 1919–26. http://dx.doi.org/10.31788/rjc.2019.1245315.

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41

Sisko, Joseph, Andrew J. Kassick, Mark Mellinger, John J. Filan, Andrew Allen, and Mark A. Olsen. "An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents1." Journal of Organic Chemistry 65, no. 5 (2000): 1516–24. http://dx.doi.org/10.1021/jo991782l.

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42

Neochoritis, Constantinos G., Despina Livadiotou, Vassilios Tsiaras, Tryfon Zarganes-Tzitzikas, and Evanthia Samatidou. "The indoleacetic acids in IMCRs: a three-component Ugi reaction involving TosMIC." Tetrahedron 72, no. 33 (2016): 5149–56. http://dx.doi.org/10.1016/j.tet.2016.07.013.

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43

Kadari, Lingaswamy, Radha Krishna Palakodety, and Lakshmi Prapurna Yallapragada. "Iodine-Catalyzed Facile Approach to Sulfones Employing TosMIC as a Sulfonylating Agent." Organic Letters 19, no. 10 (2017): 2580–83. http://dx.doi.org/10.1021/acs.orglett.7b00896.

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44

Radha Krishna, Palakodety, G. Dayaker, and P. V. Narasimha Reddy. "Diastereoselective Passerini reactions using p-toluenesulfonylmethyl isocyanide (TosMIC) as the isonitrile component." Tetrahedron Letters 47, no. 33 (2006): 5977–80. http://dx.doi.org/10.1016/j.tetlet.2006.06.044.

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45

DI SANTO, R., S. MASSA, and M. ARTICO. "ChemInform Abstract: Synthesis of Biologically Active Azoles via TosMIC. AB(39 refs.)." ChemInform 25, no. 12 (2010): no. http://dx.doi.org/10.1002/chin.199412332.

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46

SISKO, J., M. MELLINGER, P. W. SHELDRAKE, and N. H. BAINE. "ChemInform Abstract: An Efficient Method for the Synthesis of Substituted TosMIC Precursors." ChemInform 28, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199707114.

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47

Fodili, Mokhtar, Bellara Nedjar-Kolli, Bernard Garrigues, Christian Lherbet, and Pascal Hoffmann. "Synthesis of Imidazoles from Ketimines Using Tosylmethyl Isocyanide (TosMIC) Catalyzed by Bismuth Triflate." Letters in Organic Chemistry 6, no. 5 (2009): 354–58. http://dx.doi.org/10.2174/157017809788681275.

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48

Kumar Tandon, Vishnu, Vidisha Garg, Manoj Kumar, Kunwar A. Singh, Simon P. J. M. van Nispen, and Albert M. van Leusen. "A New and Convenient Route to Synthesis of Enynones and Dienones from TosMIC." HETEROCYCLES 62, no. 1 (2004): 357. http://dx.doi.org/10.3987/com-03-s(p)15.

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49

Terzidis, Michael, Constantinos A. Tsoleridis, and Julia Stephanidou-Stephanatou. "Reaction of chromone-3-carboxaldehydes with TOSMIC: synthesis of 4-(2-hydroxybenzoyl)pyrroles." Tetrahedron 63, no. 33 (2007): 7828–32. http://dx.doi.org/10.1016/j.tet.2007.05.100.

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50

Meetsma, A., H. P. Dijkstra, R. ten Have, and A. M. van Leusen. "An Unexpected Trimethylstannylpyrrole from a Stannylated Derivative of Tosylmethyl Isocyanide (TosMIC) and Chalcone." Acta Crystallographica Section C Crystal Structure Communications 52, no. 11 (1996): 2747–50. http://dx.doi.org/10.1107/s0108270196009286.

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