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Journal articles on the topic 'Chemoselective Synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Verlee, Arno, Thomas Heugebaert, Tom van der Meer, Pavel I. Kerchev, Frank Van Breusegem, and Christian V. Stevens. "A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues." Beilstein Journal of Organic Chemistry 13 (February 16, 2017): 303–12. http://dx.doi.org/10.3762/bjoc.13.33.

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For the synthesis of m-sulfamoylbenzamide analogues, small molecules which are known for their bioactivity, a chemoselective procedure has been developed starting from m-(chlorosulfonyl)benzoyl chloride. Although a chemoselective process in batch was already reported, a continuous-flow process reveals an increased selectivity at higher temperatures and without catalysts. In total, 15 analogues were synthesized, using similar conditions, with yields ranging between 65 and 99%. This is the first automated and chemoselective synthesis of m-sulfamoylbenzamide analogues.

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2

Cheng, Shuihong, Paeton L. Wantuch, Megan E. Kizer, Dustin R. Middleton, Ruitong Wang, Mikaela DiBello, Mingli Li, et al. "Glycoconjugate synthesis using chemoselective ligation." Organic & Biomolecular Chemistry 17, no. 10 (2019): 2646–50. http://dx.doi.org/10.1039/c9ob00270g.

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3

Wu, Xiao-Na, Zhi-Hao You, and Yan-Kai Liu. "Different hybridized oxygen atoms controlled chemoselective formation of oxocarbenium ions: synthesis of chiral heterocyclic compounds." Organic & Biomolecular Chemistry 16, no. 35 (2018): 6507–20. http://dx.doi.org/10.1039/c8ob01743c.

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4

Chande, Madhukar S., Kiran A. Puthamane, Pravin A. Barve, Rahul R. Khanwelkar, and Deepak S. Venkataraman. "Chemoselective synthesis of novel thiatriazolophanes." Journal of the Brazilian Chemical Society 19, no. 1 (2008): 42–52. http://dx.doi.org/10.1590/s0103-50532008000100008.

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5

Salama, P. "Chemoselective Synthesis of Functionalized Diselenides." Tetrahedron Letters 36, no. 32 (August 7, 1995): 5711–14. http://dx.doi.org/10.1016/00404-0399(50)1112u-.

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6

He, Lisheng, Yuzhu Yang, Xiaolan Liu, Guangyan Liang, Chunyan Li, Daoping Wang, and Weidong Pan. "Iodine-Mediated Oxidative Cyclization of 2-(Pyridin-2-yl)acetate Derivatives with Alkynes: Condition-Controlled Selective Synthesis of Multisubstituted Indolizines." Synthesis 52, no. 03 (October 29, 2019): 459–70. http://dx.doi.org/10.1055/s-0039-1690229.

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An iodine-mediated oxidative cyclization reaction between 2-(pyridin-2-yl)acetate derivatives and different alkynes has been developed, which provides regioselective and chemoselective syntheses of multiply substituted indolizines under modified reaction conditions. Plausible mechanisms have been proposed to explain the selective syntheses of indolizines. This protocol can be also applied to the stepwise synthesis of 2,2′-biindolizines.

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7

Kaiser, Daniel, Adriano Bauer, Miran Lemmerer, and Nuno Maulide. "Amide activation: an emerging tool for chemoselective synthesis." Chemical Society Reviews 47, no. 21 (2018): 7899–925. http://dx.doi.org/10.1039/c8cs00335a.

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8

Bressy, Cyril, Mokhtaria Belkheira, Douniazad El Abed, and Jean-Marc Pons. "Chemoselective Organoclick–Click Sequence." Synthesis 50, no. 21 (July 19, 2018): 4254–62. http://dx.doi.org/10.1055/s-0037-1610192.

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A highly chemoselective bis-triazole synthesis based on a sequence organocatalyzed click reaction/copper-catalyzed click reaction is described in this paper. A range of bis-azides react with various ketones using proline catalysis through the aryl azide moiety while the alkyl azide one remains available for a metal-catalyzed triazole synthesis.

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9

Lu, Jiaqing, Yuning Man, Yabin Zhang, Bo Lin, Qi Lin, and Zhiqiang Weng. "Copper-catalyzed chemoselective synthesis of 4-trifluoromethyl pyrazoles." RSC Advances 9, no. 53 (2019): 30952–56. http://dx.doi.org/10.1039/c9ra07694h.

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10

Chinta, Bhavani Shankar, and Beeraiah Baire. "Formal total synthesis of selaginpulvilin D." Organic & Biomolecular Chemistry 15, no. 28 (2017): 5908–11. http://dx.doi.org/10.1039/c7ob00950j.

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11

Makino, Kosho, Yumi Hasegawa, Takahide Inoue, Koji Araki, Hidetsugu Tabata, Tetsuta Oshitari, Kiyomi Ito, Hideaki Natsugari, and Hideyo Takahashi. "Chemoselective Demethylation of Methoxypyridine." Synlett 30, no. 08 (April 2, 2019): 951–54. http://dx.doi.org/10.1055/s-0037-1612427.

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A chemoselective demethylation method for various methoxypyridine derivatives has been developed. Treatment of 4-methoxypyridine with L-selectride in THF for 2 h at reflux temperature afforded 4-hydroxypyridine in good yield; no reaction to anisole occurred. The utility of our method was demonstrated by the efficient synthesis of the metabolic substances of the antiulcer agent omeprazole. Chemoselective demethylation at the site of 3,5-dimethyl-4-methoxypyridine in the presence of 4-methoxybenzimidazole was achieved.

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12

Bartoccini, F., S. Bartolucci, M. Mari, and G. Piersanti. "A simple, modular synthesis of C4-substituted tryptophan derivatives." Organic & Biomolecular Chemistry 14, no. 42 (2016): 10095–100. http://dx.doi.org/10.1039/c6ob01791f.

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13

Liu, Yihuan, Fan Yin, Xin Hu, Ning Zhu, and Kai Guo. "Protecting-group-free synthesis of thiol-functionalized degradable polyesters." Polymer Chemistry 12, no. 12 (2021): 1749–57. http://dx.doi.org/10.1039/d1py00014d.

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14

Iadonisi, Alfonso, Serena Traboni, Domenica Capasso, Emiliano Bedini, Sabrina Cuomo, Sonia Di Gaetano, and Giulia Vessella. "Switchable synthesis of glycosyl selenides or diselenides with direct use of selenium as the selenating agent." Organic Chemistry Frontiers 8, no. 8 (2021): 1823–29. http://dx.doi.org/10.1039/d1qo00045d.

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15

Furuyama, Taniyuki, Kazuya Maeda, Hajime Maeda, and Masahito Segi. "Chemoselective Synthesis of Aryloxy-Substituted Phthalocyanines." Journal of Organic Chemistry 84, no. 21 (October 10, 2019): 14306–12. http://dx.doi.org/10.1021/acs.joc.9b02126.

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16

Ferrié,, Laurent, Sébastien Reymond, Patrice Capdevielle, and Janine Cossy. "Formal Chemoselective Synthesis of Leucascandrolide A." Organic Letters 9, no. 13 (June 2007): 2461–64. http://dx.doi.org/10.1021/ol070670a.

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17

Lopes, Rosangela, Cláudio Lopes, Marcelo Nery, Mariangela Azevedo, Jari Cardoso, and Glaucia Slana. "A New Chemoselective Synthesis of Brombuterol." Synthesis 48, no. 03 (January 19, 2016): 462. http://dx.doi.org/10.1055/s-0035-1560401.

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18

Lopes, Rosangela, Cláudio Lopes, Marcelo Nery, Mariangela Azevedo, Jari Cardoso, and Glaucia Slana. "A New Chemoselective Synthesis of Brombuterol." Synthesis 2007, no. 10 (May 2, 2007): 1471–74. http://dx.doi.org/10.1055/s-2007-966044.

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19

Takasu, A., Y. Shibata, Y. Narukawa, and T. Hirabayashi. "Polyester Synthesis via Chemoselective Dehydration Polycondensations." Synfacts 2007, no. 4 (April 2007): 0378. http://dx.doi.org/10.1055/s-2007-968308.

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20

Ballini, Roberto, Roberto Castagnani, and Marino Petrini. "Chemoselective synthesis of functionalized conjugated nitroalkenes." Journal of Organic Chemistry 57, no. 7 (March 1992): 2160–62. http://dx.doi.org/10.1021/jo00033a045.

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21

Li, Xinmin, Fangfang Feng, Changyue Ren, Yong Teng, Qinghong Hu, and Zeli Yuan. "Base-Controlled One-Pot Chemoselective Suzuki–Miyaura Reactions for the Synthesis of Unsymmetrical Terphenyls." Synlett 30, no. 19 (November 4, 2019): 2131–35. http://dx.doi.org/10.1055/s-0039-1690227.

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We report a chemoselective Suzuki–Miyaura reaction protocol of using bromophenyl fluorosulfonate as building block for the preparation of unsymmetrical terphenyls. The chemoselective cross-coupling of bromophenyl fluorosulfonate and arylboronic acids can be achieved by controlling base species without using any ligands. Under this methodology, various of m- and p-unsymmetrical terphenyls were obtained in moderate to good yields.

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22

Tak, Raj K., Fuyuki Amemiya, Hidetoshi Noda, and Masakatsu Shibasaki. "Generation and application of Cu-bound alkyl nitrenes for the catalyst-controlled synthesis of cyclic β-amino acids." Chemical Science 12, no. 22 (2021): 7809–17. http://dx.doi.org/10.1039/d1sc01419f.

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23

Montoir, David, Mehdi Amoura, Zine El Abidine Ababsa, T. M. Vishwanatha, Expédite Yen-Pon, Vincent Robert, Massimiliano Beltramo, et al. "Synthesis of aryl-thioglycopeptides through chemoselective Pd-mediated conjugation." Chemical Science 9, no. 46 (2018): 8753–59. http://dx.doi.org/10.1039/c8sc02370k.

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24

Nicolas, Lionel, Alexey N. Butkevich, Amandine Guérinot, Andrei Corbu, Sébastien Reymond, and Janine Cossy. "Synthesis of complex oxygenated heterocycles." Pure and Applied Chemistry 85, no. 6 (March 27, 2013): 1203–13. http://dx.doi.org/10.1351/pac-con-12-09-15.

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Versatile and chemoselective preparation of substituted oxygenated heterocycles is described. Highly diastereoselective metal-catalyzed syntheses of trans-2,6- and cis-2,6-disubstituted tetrahydropyrans (THPs) are presented, along with an easy one-pot access to various ring size benzoannulated spiroketals.

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25

Mal, Dipakranjan, and Joyeeta Roy. "A regioselective facile synthesis of furo[3,4-b]carbazolones: application to the total synthesis of mafaicheenamine E and claulansine D." Organic & Biomolecular Chemistry 13, no. 22 (2015): 6344–52. http://dx.doi.org/10.1039/c5ob00575b.

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26

Aziz, Jessy, Jean-Daniel Brion, Mouad Alami, and Abdallah Hamze. "Synthesis of benzofulvenes through chemoselective Sonogashira and Barluenga couplings of ortho ethynyl-N-tosylhydrazones and cycloisomerization." RSC Advances 5, no. 91 (2015): 74391–98. http://dx.doi.org/10.1039/c5ra14459k.

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27

Paulsen, Marianne Hagensen, Magnus Engqvist, Dominik Ausbacher, Morten Bøhmer Strøm, and Annette Bayer. "Efficient and scalable synthesis of α,α-disubstituted β-amino amides." Organic & Biomolecular Chemistry 14, no. 31 (2016): 7570–78. http://dx.doi.org/10.1039/c6ob01219a.

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28

N., Narendra, Vishwanatha M. Thimmalapura, Basavaprabhu Hosamani, Girish Prabhu, L. Roopesh Kumar, and Vommina V. Sureshbabu. "Thioacids – synthons for amide bond formation and ligation reactions: assembly of peptides and peptidomimetics." Organic & Biomolecular Chemistry 16, no. 19 (2018): 3524–52. http://dx.doi.org/10.1039/c8ob00512e.

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The synthesis of α-amino thioacids and peptide thioacids and their applications in chemoselective amide bond formation, ligation of peptides/proteins/glycopeptides and synthesis of peptidomimetics are reviewed.

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29

Sarkar, Satavisha, Deb K. Das, and Abu T. Khan. "Synthesis of fully-substituted pyridines and dihydropyridines in a highly chemoselective manner utilizing a multicomponent reaction (MCR) strategy." RSC Adv. 4, no. 96 (2014): 53752–60. http://dx.doi.org/10.1039/c4ra08237k.

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30

Ma, Zhongxiao, Xiao Hu, Yanni Li, Deqiang Liang, Ying Dong, Baoling Wang, and Weili Li. "Electrochemical oxidative synthesis of 1,3,4-thiadiazoles from isothiocyanates and hydrazones." Organic Chemistry Frontiers 8, no. 10 (2021): 2208–14. http://dx.doi.org/10.1039/d1qo00168j.

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31

Lin, Wenwei, Praneeth Karanam, and Ganapuram Reddy. "Strategic Exploitation of the Wittig Reaction: Facile Synthesis of Heteroaromatics and Multifunctional Olefins." Synlett 29, no. 20 (August 2, 2018): 2608–22. http://dx.doi.org/10.1055/s-0037-1610486.

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In this account, our group’s efforts towards exploring new substrates as precursors for the Wittig reaction have been discussed. Several new strategies developed by our group for the generation of requisite ylides for the Wittig reaction are highlighted. The idea behind the development of some chemoselective and diversity-oriented strategies are discussed in detail in a progressive manner. These strategies encompass a wide range of substrates that are employed for the synthesis of an array of heterocycles and multifunctional olefins and present a huge scope for their application on an industrial level.1 Introduction2 Development of New Methods to Effect Intramolecular Wittig Reaction3 Development of a Catalytic Wittig Reaction4 New Synthesis of Bis-Heteroarenes5 Direct β-Acylation of 2-Arylidene-1,3-indandiones6 Doubly Chemoselective Protocol for the Diversity-Oriented Synthesis of Coumarin Derivatives7 Conclusion

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32

Kang, Jing-Wen, Xiang Li, Fei-Yu Chen, Yuan Luo, Shu-Cang Zhang, Bin Kang, Cheng Peng, Xu Tian, and Bo Han. "Protecting group-directed annulations of tetra-substituted oxindole olefins and sulfur ylides: regio- and chemoselective synthesis of cyclopropane- and dihydrofuran-fused spirooxindoles." RSC Advances 9, no. 22 (2019): 12255–64. http://dx.doi.org/10.1039/c9ra02192b.

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33

Maleki, Behrooz, Saba Hemmati, Alireza Sedrpoushan, Samaneh Sedigh Ashrafi, and Hojat Veisi. "Selective synthesis of sulfoxides and sulfones from sulfides using silica bromide as the heterogeneous promoter and hydrogen peroxide as the terminal oxidant." RSC Adv. 4, no. 76 (2014): 40505–10. http://dx.doi.org/10.1039/c4ra06132b.

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34

Veisi, Hojat, Behrooz Maleki, Mona Hamelian, and Samaneh Sedigh Ashrafi. "Chemoselective hydration of nitriles to amides using hydrated ionic liquid (IL) tetrabutylammonium hydroxide (TBAH) as a green catalyst." RSC Advances 5, no. 9 (2015): 6365–71. http://dx.doi.org/10.1039/c4ra09864a.

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35

Abe, Hideki, Satoko Itaya, Kei Sasaki, Toyoharu Kobayashi, and Hisanaka Ito. "Total synthesis of the proposed structure of a polyketide from Phialomyces macrosporus." Chemical Communications 51, no. 17 (2015): 3586–89. http://dx.doi.org/10.1039/c5cc00129c.

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Total synthesis of the proposed structure of a polyketide isolated from Phialomyces macrosporus was accomplished. This synthesis features chemoselective epoxidation, regioselective epoxide ring opening, chemo- and diastereoselective dihydroxylation, and vinylation of lactone accompanied by the formation of a furan ring.

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36

Ma, Yu-Chuan, Jin-Yun Luo, Shi-Chu Zhang, Shu-Hui Lu, Guang-Fen Du, and Lin He. "An N-heterocyclic carbene-catalyzed switchable reaction of 9-(trimethylsilyl)fluorene and aldehydes: chemoselective synthesis of dibenzofulvenes and fluorenyl alcohols." Organic & Biomolecular Chemistry 19, no. 16 (2021): 3717–21. http://dx.doi.org/10.1039/d1ob00065a.

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37

Wang, Darui, Bing Ma, Bo Wang, Chen Zhao, and Peng Wu. "One-pot synthesized hierarchical zeolite supported metal nanoparticles for highly efficient biomass conversion." Chemical Communications 51, no. 82 (2015): 15102–5. http://dx.doi.org/10.1039/c5cc06212h.

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38

Yang, Qing, Yilin Zhang, Wei Zeng, Zheng-Chao Duan, Xinxin Sang, and Dawei Wang. "Merrifield resin-supported quinone as an efficient biomimetic catalyst for metal-free, base-free, chemoselective synthesis of 2,4,6-trisubstituted pyridines." Green Chemistry 21, no. 20 (2019): 5683–90. http://dx.doi.org/10.1039/c9gc02409c.

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39

Panwar, Rahul, Shally Shally, Ranjay Shaw, Amr Elagamy, and Ramendra Pratap. "Chemoselective synthesis of m-teraryls through ring transformation of 2H-pyran-2-ones by 2-(1-arylethylidene)-malononitriles." Organic & Biomolecular Chemistry 16, no. 46 (2018): 8994–9002. http://dx.doi.org/10.1039/c8ob02370k.

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40

Nascimento, Thiana Santiago, Esther Faria Braga, Giselle Cristina Casaes Gomes, William Romão Batista, André Luís Mazzei Albert, Rosangela Sabbatini Capella Lopes, and Claudio Cerqueira Lopes. "Synthesis of natural 1-O-alkylglycerols: a study on the chemoselective opening of the epoxide ring by onium quaternary salts (N and P) and ionic liquids." RSC Advances 10, no. 2 (2020): 1050–54. http://dx.doi.org/10.1039/c9ra09217j.

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41

Krishnappa, Lokesh, and HariPrasad Suresh. "A Novel Regiospecific Synthesis of 1-Chloro-2-arylcyclohexenes." Organic Chemistry International 2014 (July 10, 2014): 1–6. http://dx.doi.org/10.1155/2014/871595.

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An efficient high yielding chemoselective synthesis of eleven novel 1-chloro-2-arylcyclohexenes employing the Suzuki cross coupling of 1-bromo-2-chlorocyclohexene with eleven different aryl boronic acids and Pd(dppf)Cl2·CH2Cl2 catalyst is reported.

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42

Lin, Shengjia, Lucia Wang, Negin Aminoleslami, Yanting Lao, Chelsea Yagel, and Abhishek Sharma. "A modular and concise approach to MIDA acylboronates via chemoselective oxidation of unsymmetrical geminal diborylalkanes: unlocking access to a novel class of acylborons." Chemical Science 10, no. 17 (2019): 4684–91. http://dx.doi.org/10.1039/c9sc00378a.

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43

Chatterjee, Basujit, and Chidambaram Gunanathan. "The ruthenium-catalysed selective synthesis of mono-deuterated terminal alkynes." Chemical Communications 52, no. 24 (2016): 4509–12. http://dx.doi.org/10.1039/c6cc01401a.

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A highly efficient catalytic system is reported for chemoselective synthesis of mono-deuterated terminal alkynes using deuterium oxide in which the reaction proceeds via Ru–acetylide intermediates formed by selective activation of the sp-CH bond.

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44

Aksenov, Alexander V., Vladislav Khamraev, Nicolai A. Aksenov, Nikita K. Kirilov, Dmitriy A. Domenyuk, Vladimir A. Zelensky, and Michael Rubin. "Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles." RSC Advances 9, no. 12 (2019): 6636–42. http://dx.doi.org/10.1039/c9ra00976k.

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45

Chandrasekar, Selvaraj, and Govidasamy Sekar. "An efficient synthesis of iminoquinones by a chemoselective domino ortho-hydroxylation/oxidation/imidation sequence of 2-aminoaryl ketones." Organic & Biomolecular Chemistry 14, no. 11 (2016): 3053–60. http://dx.doi.org/10.1039/c5ob02659h.

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46

Chu, Xue-Qiang, Danhua Ge, Teck-Peng Loh, and Zhi-Liang Shen. "Oxidant-directed chemoselective sulfonylation and sulfonyloximation of alkenes via cleaving the C–S bond in TosMIC." Organic Chemistry Frontiers 6, no. 6 (2019): 835–40. http://dx.doi.org/10.1039/c8qo01346b.

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47

Reimann, Sebastian, Silvio Parpart, Peter Ehlers, Muhammad Sharif, Anke Spannenberg, and Peter Langer. "Synthesis of tetraarylpyridines by chemo-selective Suzuki–Miyaura reactions of 3,5-dibromo-2,6-dichloropyridine." Organic & Biomolecular Chemistry 13, no. 24 (2015): 6832–38. http://dx.doi.org/10.1039/c5ob00866b.

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48

Noda, Hidetoshi, and Jeffrey W. Bode. "Synthesis and chemoselective ligations of MIDA acylboronates with O-Me hydroxylamines." Chem. Sci. 5, no. 11 (2014): 4328–32. http://dx.doi.org/10.1039/c4sc00971a.

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49

C. Veronese, Augusto, Chiara B. Vicentini, Maurizio Manfrini, Manuela Mazzanti, Monica Manferdini, and Carlo F. Morelli. "Chemoselective Synthesis of 3- and 5-Pyrazolylacetates." HETEROCYCLES 53, no. 6 (2000): 1285. http://dx.doi.org/10.3987/com-00-8871.

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50

Rawat, Ajay Singh, Sachin Pande, Nilay Bhatt, Raju Kharatkar, Chandrakant Belwal, and Anand Vardhan. "Synthesis of Donepezil Hydrochloride via Chemoselective Hydrogenation." Organic Process Research & Development 17, no. 12 (May 6, 2013): 1617. http://dx.doi.org/10.1021/op400007p.

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