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Journal articles on the topic 'Passerini Reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 June 2024

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1

Ichikawa, Yoshiyasu, Toshiki Yamasaki, Keisuke Nakanishi, Yutaro Udagawa, Seijiro Hosokawa, and Toshiya Masuda. "Bioinspired Synthesis of the Central Core of Halichonadin H: The Passerini Reaction in a Hypothetical Biosynthesis of Marine Natural Products." Synthesis 51, no. 11 (March 14, 2019): 2305–10. http://dx.doi.org/10.1055/s-0037-1610867.

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A pathway is proposed for the biosynthesis of the unique homodimeric terpene, halichonadin H. The proposed biosynthetic pathway involves two key Passerini reactions of eudesmane-type terpene isocyanides. The Passerini reaction of a model terpene isocyanide and formaldehyde afforded an α-hydroxy acetamide, which was further subjected to oxidation and a second Passerini reaction. This reaction sequence furnished an α-hydroxy malonamide connected with two identical terpene units which is the identical structural motif found in halichonadin H.

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2

Onwukamike, Kelechukwu Nnabuike, Stéphane Grelier, Etienne Grau, Henri Cramail, and Michael A. R. Meier. "On the direct use of CO2in multicomponent reactions: introducing the Passerini four component reaction." RSC Advances 8, no. 55 (2018): 31490–95. http://dx.doi.org/10.1039/c8ra07150k.

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We introduce a novel isocyanide-based multicomponent reaction, the Passerini four component reaction (P-4CR), by replacing the carboxylic acid component of a conventional Passerini three component reaction (P-3CR) with an alcohol and CO₂.

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3

Boukis, Andreas C., Baptiste Monney, and Michael A. R. Meier. "Synthesis of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones via sequential Biginelli and Passerini reactions." Beilstein Journal of Organic Chemistry 13 (January 9, 2017): 54–62. http://dx.doi.org/10.3762/bjoc.13.7.

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The Biginelli reaction was combined with the Passerini reaction for the first time in a sequential multicomponent tandem reaction approach. After evaluation of all possible linker components and a suitable solvent system, highly functionalized dihydropyrimidone–α-acyloxycarboxamide compounds were obtained in good to excellent yields. In a first reaction step, different 3,4-dihydropyrimidin-2(1H)-one acids were synthesized, isolated and fully characterized. These products were subsequently used in a Passerini reaction utilizing a dichloromethane/dimethyl sulfoxide solvent mixture. By variation of the components in both multicomponent reactions, a large number of structurally diverse compounds could be synthesized. In addition, a one-pot Biginelli–Passerini tandem reaction was demonstrated. All products were carefully characterized via 1D and 2D NMR as well as IR and HRMS.

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4

Zhao, Long, Mao-Lin Yang, Min Liu, and Ming-Wu Ding. "New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence." Beilstein Journal of Organic Chemistry 18 (March 4, 2022): 286–92. http://dx.doi.org/10.3762/bjoc.18.32.

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A new efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines via sequential Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reaction has been developed. The three-component Passerini reactions of 2-azidobenzaldehydes 1, benzoic acid (2), and isocyanides 3 produced the azide intermediates 4, which were treated sequentially with triphenylphosphine, isocyanates (or CS2), and secondary amines to give polysubstituted 3,4-dihydroquinazolines 8 and 4H-3,1-benzothiazines 11 in good overall yields through consecutive Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reactions.

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5

Shaabani, Ahmad, Hassan Farhid, Mohammad Mahdi Rostami, and Behrouz Notash. "Synthesis of Depsipeptides via Isocyanide-Based Consecutive Bargellini–Passerini Multicomponent Reactions." SynOpen 05, no. 03 (June 22, 2021): 167–72. http://dx.doi.org/10.1055/a-1533-3823.

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AbstractAn efficient and straightforward approach has been established for the preparation of a new class of depsipeptide structures via isocyanide-based consecutive Bargellini–Passerini multicomponent reactions. 3-Carboxamido-isobutyric acids bearing an amide bond were obtained via Bargellini multicomponent reaction from isocyanides, acetone, and chloroform in the presence of sodium hydroxide. Next, via a Passerini multicomponent-reaction strategy, a new class of depsipeptides was synthesized using the Bargellini reaction products, isocyanides, and aldehydes. The depsipeptides thus prepared have more flexible structures than their pseudopeptidic analogues.

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6

Neo, Ana G., and Carlos F. Marcos. "Pyrrolidinodiones in Enol-Ugi, Enol-Passerini, and Anomalous Enol-Passerini Condensations." Proceedings 9, no. 1 (November 19, 2018): 6. http://dx.doi.org/10.3390/ecsoc-22-05864.

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In continuation of our recent research on the development of novel multicomponent reactions with isocyanides, we have used, for the first time, enols as the acid components in Ugi- and Passerini-type reactions. Thus, electron-poor pyrrolidinodiones react with aldehydes, amines, and isocyanides to give the enaminic four-component adducts. Conversely, in the absence of the amine component, careful control of the reaction conditions allows the involvement of one or two molecules of isocyanide to afford, selectively, either Passerini-type or pseudo-enol-Ugi-type products. These unprecedented condensations of isocyanides, aldehydes, amines, and 4-substituted pyrrolidine-2,3-diones constitute an excellent strategy for the preparation of new biologically relevant pyrrolidinones having peptidic or pseudo-peptidic groups on carbon 3.

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7

Haven, Joris J., Evelien Baeten, Jonathan Claes, Joke Vandenbergh, and Tanja Junkers. "High-throughput polymer screening in microreactors: boosting the Passerini three component reaction." Polymer Chemistry 8, no. 19 (2017): 2972–78. http://dx.doi.org/10.1039/c7py00360a.

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The Passerini three-component reaction (Passerini-3CR) has been studied via on-line microreactor/electrospray ionisation mass spectrometry (MRT/ESI-MS) reaction monitoring to demonstrate the high-throughput screening potential of microreactors for macromolecular design.

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8

Reza Kazemizadeh, Ali, and Ali Ramazani. "Synthetic Applications of Passerini Reaction." Current Organic Chemistry 16, no. 4 (February 1, 2012): 418–50. http://dx.doi.org/10.2174/138527212799499868.

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9

Giustiniano, Mariateresa, Lisa Moni, Gian Tron, Luca Sangaletti, Sveva Pelliccia, Andrea Basso, and Ettore Novellino. "Interrupted Ugi and Passerini Reactions: An Underexplored Treasure Island." Synthesis 50, no. 18 (August 15, 2018): 3549–70. http://dx.doi.org/10.1055/s-0037-1610193.

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The formation of the key short-lived intermediate nitrilium ion in the Passerini and Ugi reactions was recognized early in the discovery of these two-multicomponent transformations. Surprisingly, the idea of intramolecularly intercepting it, eluding the attack by the carboxylate, and thus interrupting the normal course of the reaction, was missed by chemists for several decades. In this review we describe, in an exhaustive manner, the reported synthetic approaches, which can be categorized as interrupted Passerini/Ugi reactions. Besides, the clear goal of this review is to show the potential of these transformations, whilst highlighting the underexplored combinations of reagents toward the identification of novel interrupted Passerini/Ugi reactions.1 Introduction2 The Interrupted Ugi Reaction2.1 The Interrupting Functional Group is Present on the Amine Reactant2.2 The Interrupting Functional Group is Present on the Isocyanide Reactant2.3 The Interrupting Functional Group is Present on the Carbonyl Reactant3 The Interrupted Passerini Reaction3.1 The Interrupting Functional Group is Present on the Carbonyl Reactant3.2 The Interrupting Functional Group is Present on the Isocyanide Reactant4 Conclusions and Future Outlook

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10

Andreana, Peter R., Chang C. Liu, and Stuart L. Schreiber. "Stereochemical Control of the Passerini Reaction." Organic Letters 6, no. 23 (November 2004): 4231–33. http://dx.doi.org/10.1021/ol0482893.

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11

Wang, Shi-Xin, Mei-Xiang Wang, De-Xian Wang, and Jieping Zhu. "Catalytic Enantioselective Passerini Three-Component Reaction." Angewandte Chemie International Edition 47, no. 2 (January 2008): 388–91. http://dx.doi.org/10.1002/anie.200704315.

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12

Wang, Shi-Xin, Mei-Xiang Wang, De-Xian Wang, and Jieping Zhu. "Catalytic Enantioselective Passerini Three-Component Reaction." Angewandte Chemie 120, no. 2 (January 2008): 394–97. http://dx.doi.org/10.1002/ange.200704315.

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13

Żądło-Dobrowolska, Anna, Dominik Koszelewski, Daniel Paprocki, Arleta Madej, Monika Wilk, and Ryszard Ostaszewski. "Enzyme-Promoted Asymmetric Tandem Passerini Reaction." ChemCatChem 9, no. 15 (June 20, 2017): 3047–53. http://dx.doi.org/10.1002/cctc.201700427.

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14

Pertejo, Pablo, Andrea Sancho-Medina, Tomás Hermosilla, Beatriz González-Saiz, Javier Gómez-Ayuso, Roberto Quesada, Daniel Moreno, Israel Carreira-Barral, and María García-Valverde. "Keto-Enol Tautomerism in Passerini and Ugi Adducts." Molecules 26, no. 4 (February 9, 2021): 919. http://dx.doi.org/10.3390/molecules26040919.

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The use of arylglyoxal as starting material in Passerini and Ugi reactions affords β-ketoamides. This has allowed to study keto-enol tautomerism in these systems and assess the way in which the presence of acyloxy or aminoacyl groups bound to the C2 position affects such tautomerism, and to investigate the reactivity of both the enol and carbonyl forms. In this work we also prove the versatility of the Passerini reaction, since depending on the conditions to which the corresponding adducts are subjected different products of synthetic interest can be obtained.

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15

Maeda, Satoshi, Shinsuke Komagawa, Masanobu Uchiyama, and Keiji Morokuma. "Finding Reaction Pathways for Multicomponent Reactions: The Passerini Reaction is a Four-Component Reaction." Angewandte Chemie International Edition 50, no. 3 (December 17, 2010): 644–49. http://dx.doi.org/10.1002/anie.201005336.

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16

Maeda, Satoshi, Shinsuke Komagawa, Masanobu Uchiyama, and Keiji Morokuma. "Finding Reaction Pathways for Multicomponent Reactions: The Passerini Reaction is a Four-Component Reaction." Angewandte Chemie 123, no. 3 (December 17, 2010): 670–75. http://dx.doi.org/10.1002/ange.201005336.

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17

Banfi, Luca, Andrea Basso, Chiara Lambruschini, Lisa Moni, and Renata Riva. "The 100 facets of the Passerini reaction." Chemical Science 12, no. 47 (2021): 15445–72. http://dx.doi.org/10.1039/d1sc03810a.

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18

Oelmann, S., and M. A. R. Meier. "Synthesis and unimolecular micellar behavior of amphiphilic star-shaped block copolymers obtained via the Passerini three component reaction." RSC Advances 7, no. 71 (2017): 45195–99. http://dx.doi.org/10.1039/c7ra08982a.

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19

Chandgude, Ajay L., and Alexander Dömling. "An efficient Passerini tetrazole reaction (PT-3CR)." Green Chemistry 18, no. 13 (2016): 3718–21. http://dx.doi.org/10.1039/c6gc00910g.

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20

Andrade, Carlos, Sayuri Takada, Paulo Suarez, and Melquizedeque Alves. "Revisiting the Passerini Reaction under Eco-Friendly Reaction Conditions." Synlett 2006, no. 10 (June 2006): 1539–42. http://dx.doi.org/10.1055/s-2006-941606.

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21

Salami, Sodeeq Aderotimi, Meloddy Manyeruke, Xavier Siwe-Noundou, and Rui Werner Maçedo Krause. "Immobilized Sulfuric Acid on Silica Gel as Highly Efficient and Heterogeneous Catalyst for the One-Pot Synthesis of Novel α-Acyloxycarboxamides in Aqueous Media." International Journal of Molecular Sciences 23, no. 17 (August 23, 2022): 9529. http://dx.doi.org/10.3390/ijms23179529.

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The application of immobilized sulfuric acid on silica gel (H2SO4-SiO2) as an efficient and easily reusable solid catalyst was explored in the synthesis of novel α-acyloxycarboxamide derivatives via a Passerini reaction of benzoic acid, aldehyde/ketone, and isocyanides. The Passerini adducts were obtained in high to excellent yields within 10 min in aqueous media under catalytic conditions. The key advantages of the process include a short reaction time, high yields, the catalyst’s low cost, and the catalyst’s reusability.

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22

Fan, Xuesen, Yanzhen Li, Xinying Zhang, Guirong Qu, and Jianji Wang. "A novel and green version of the Passerini reaction in an ionic liquid ([bmim][BF4])." Canadian Journal of Chemistry 84, no. 5 (May 1, 2006): 794–99. http://dx.doi.org/10.1139/v06-070.

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The Passerini three-component condensation among a carboxylic acid (1), an aldehyde or ketone (2), and an isocyanide (3) was carried out for the first time in an ionic liquid, [bmim][BF4], and a series of acyloxycarboxamides were obtained through this reaction. The method presented herein has the advantages of high efficiency, a greener nature, and a simple operational procedure. Moreover, the ionic liquid can be easily recovered and reused for several runs without obvious loss of efficiency.Key words: Passerini reaction, acyloxycarboxamides, ionic liquid, green synthesis.

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23

Zhang, Jian, Shao-Xia Lin, Dao-Juan Cheng, Xin-Yuan Liu, and Bin Tan. "Phosphoric Acid-Catalyzed Asymmetric Classic Passerini Reaction." Journal of the American Chemical Society 137, no. 44 (October 30, 2015): 14039–42. http://dx.doi.org/10.1021/jacs.5b09117.

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24

Bousquet, Till, Mouhamad Jida, Mohamad Soueidan, Rebecca Deprez-Poulain, Francine Agbossou-Niedercorn, and Lydie Pelinski. "Fast and efficient solvent-free Passerini reaction." Tetrahedron Letters 53, no. 3 (January 2012): 306–8. http://dx.doi.org/10.1016/j.tetlet.2011.11.028.

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25

Chandgude, Ajay L., and Alexander Dömling. "Unconventional Passerini Reaction toward α-Aminoxy-amides." Organic Letters 18, no. 24 (December 2016): 6396–99. http://dx.doi.org/10.1021/acs.orglett.6b03293.

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26

Vlahoviček-Kahlina, Kristina, Mario Vazdar, Andreja Jakas, Vilko Smrečki, and Ivanka Jerić. "Synthesis of Glycomimetics by Diastereoselective Passerini Reaction." Journal of Organic Chemistry 83, no. 21 (October 16, 2018): 13146–56. http://dx.doi.org/10.1021/acs.joc.8b01874.

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27

Jee, Jo-Ann, Shuang Song, and Jonathan G. Rudick. "Enhanced reactivity of dendrons in the Passerini three-component reaction." Chemical Communications 51, no. 25 (2015): 5456–59. http://dx.doi.org/10.1039/c4cc10091c.

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28

Vavsari, Vaezeh Fathi, Pegah Shakeri, and Saeed Balalaie. "Application of Chiral Isocyanides in Multicomponent Reactions." Current Organic Chemistry 24, no. 2 (April 15, 2020): 162–83. http://dx.doi.org/10.2174/1385272824666200110095120.

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As one of the most important building blocks in organic synthesis, isocyanides come in for a wide range of transformations owing mostly to their unusual terminal carbon center adsorbed electrophiles, reacted with nucleophiles, get involved in radical reactions and coordinated with metal centers. The distinctive feature of isocyanide is its ready willingness to participate in multicomponent reactions (MCRs). MCRs represent a great tool in organic synthesis for the construction of new lead structures in a single procedure introducing both structural diversity and molecular complexity in only one step. Isocyanide-based multicomponent reactions (IMCRs) have become a powerful approach for the synthesis of complex molecules providing high degree of atom and bond economy under very mild reaction conditions. The use of enantiomerically pure isocyanides can, in principle, bring about two advantages: (i) the possibility to obtain a stereochemically diverse adduct, controlling the absolute configuration of the starting isocyanide; and (ii) the possibility to induce diastereoselection in the multicomponent reaction. The most commonly-used IMCRs are the Ugi and Passerini reactions. Many published reviews have focused on the Ugi and Passerini reactions from different viewpoints, but this review describes advances in the application of chiral isocyanides in MCRs. The rationale for applying such diversity generating chemistries is also discussed.

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29

Marchi, Pietro, Wei Wang, Cristián Puig, Ander Martin, Tullio Crovetto, Jalel Labidi, Renata Riva, Dario Cavallo, and Lisa Moni. "Synthesis of symmetric bis-α-ketoamides from renewable starting materials and comparative study of their nucleating efficiency in PLLA." RSC Advances 13, no. 8 (2023): 4994–5001. http://dx.doi.org/10.1039/d2ra07934h.

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30

Wang, Guannan, Raju Raju, Kiho Cho, Sandy Wong, B. Gangadhara Prusty, and Martina H. Stenzel. "3D printed nanocomposites using polymer grafted graphene oxide prepared by multicomponent Passerini reaction." Polymer Chemistry 11, no. 45 (2020): 7253–63. http://dx.doi.org/10.1039/d0py01286f.

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31

Gola, Gabriel F., Gabriela M. Di Venosa, Daniel A. Sáenz, Gustavo H. Calvo, Gabriela M. Cabrera, Adriana G. Casas, and Javier A. Ramírez. "Synthesis of chemically diverse esters of 5-aminolevulinic acid for photodynamic therapy via the multicomponent Passerini reaction." RSC Advances 6, no. 92 (2016): 89492–98. http://dx.doi.org/10.1039/c6ra15832c.

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32

Lin, Wenhai, Tingting Sun, Min Zheng, Zhigang Xie, Yubin Huang, and Xiabin Jing. "Synthesis of cross-linked polymers via multi-component Passerini reaction and their application as efficient photocatalysts." RSC Adv. 4, no. 48 (2014): 25114–17. http://dx.doi.org/10.1039/c4ra02666g.

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33

Zahoor, Ameer F., Sarah Thies, and Uli Kazmaier. "A straightforward approach towards combined α-amino and α-hydroxy acids based on Passerini reactions." Beilstein Journal of Organic Chemistry 7 (September 19, 2011): 1299–303. http://dx.doi.org/10.3762/bjoc.7.151.

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Complex amino acids with an α-acyloxycarbonyl functionality in the side chain are easily available through epoxide opening by chelated enolates and subsequent oxidation/Passerini reaction. This protocol works with both, aldehyde and ketone intermediates, as long as the ketones are activated by electron-withdrawing groups. In principle Ugi reactions are also possible, allowing the generation of diamino acid derivatives.

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34

Xiong, Jun, Qi-Xun Feng, Zhi-Ying Mu, Gang Yao, Jia-An Zhang, Hui-Ting He, and Yong-Long Pang. "Efficient Synthesis of 4H-3,1-Benzoxazine Derivatives via One-Pot Sequential Passerini-Azide/Palladium-Catalyzed Azide–Isocyanide Coupling/Cyclization Reaction." Synlett 31, no. 10 (February 18, 2020): 1003–6. http://dx.doi.org/10.1055/s-0039-1690831.

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A new, one-pot method for the synthesis of 4H-3,1-benzoxazine derivatives has been developed. The Passerini-azide reactions of 2-azidobenzaldehydes, trimethylsilyl azide, and isocyanides produced azide intermediate without separation, which then reacted with isocyanides to give 4H-3,1-benzoxazine derivatives via a tandem one-pot palladium-catalyzed azide–isocyanide coupling/cyclization reaction in moderate to good yields.

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35

Lin, Wenhai, Tingting Sun, Zhigang Xie, Jingkai Gu, and Xiabin Jing. "A dual-responsive nanocapsule via disulfide-induced self-assembly for therapeutic agent delivery." Chemical Science 7, no. 3 (2016): 1846–52. http://dx.doi.org/10.1039/c5sc03707g.

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36

Suć, Josipa, Danijela Barić, and Ivanka Jerić. "Multicomponent synthesis of hydrazino depsipeptides." RSC Advances 6, no. 102 (2016): 99664–75. http://dx.doi.org/10.1039/c6ra23317a.

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37

Kumar, Banty, Jyotirmoy Maity, Bhawani Shankar, Sandeep Kumar, Kavita, and Ashok K. Prasad. "Synthesis of d-glycopyranosyl depsipeptides using Passerini reaction." Carbohydrate Research 500 (February 2021): 108236. http://dx.doi.org/10.1016/j.carres.2021.108236.

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38

Glavaš, Mladena, Matija Gredičak, and Ivanka Jerić. "Enediyne-Comprising Amino Aldehydes in the Passerini Reaction." ACS Combinatorial Science 20, no. 3 (January 17, 2018): 151–55. http://dx.doi.org/10.1021/acscombsci.7b00167.

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39

Adib, Mehdi, Ehsan Sheikhi, and Marjan Azimzadeh. "A new modification of the Passerini reaction: a one-pot synthesis of α-acyloxyamides via sequential Kornblum oxidation/Passerini reaction." Tetrahedron Letters 56, no. 15 (April 2015): 1933–36. http://dx.doi.org/10.1016/j.tetlet.2015.02.007.

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40

Lyu, Longyun, Han Xie, Huaixue Mu, Qijie He, Zhaoxiang Bian, and Jun Wang. "AlCl3-catalyzed O-alkylative Passerini reaction of isocyanides, cinnamaldehydes and various aliphatic alcohols for accessing α-alkoxy-β,γ-enamides." Organic Chemistry Frontiers 2, no. 7 (2015): 815–18. http://dx.doi.org/10.1039/c5qo00106d.

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41

Moni, Lisa, Luca Banfi, Daniele Cartagenova, Andrea Cavalli, Chiara Lambruschini, Elisa Martino, Romano V. A. Orru, et al. "Zinc(ii)-mediated diastereoselective Passerini reactions of biocatalytically desymmetrised renewable inputs." Organic Chemistry Frontiers 7, no. 2 (2020): 380–98. http://dx.doi.org/10.1039/c9qo00773c.

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A chiral aldehyde, obtained in both enantiomeric forms from renewable 2,5-Bis(hydroxymethyl)tetrahydrofuran by a chemoenzymatic procedure, was submitted to a modified diastereoselective Passerini reaction employing zinc dicarboxylates.

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42

Paprocki, Daniel, Dominik Koszelewski, Peter Walde, and Ryszard Ostaszewski. "Efficient Passerini reactions in an aqueous vesicle system." RSC Advances 5, no. 124 (2015): 102828–35. http://dx.doi.org/10.1039/c5ra22258c.

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The formation of α-acyloxy carboxamides from a carboxylic acid, an aldehyde and an isocyanide (Passerini reaction) was investigated in aqueous solution in the presence of different types of surfactants.

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43

Schmidt, Sonja, Miriam Koldevitz, Janina-Miriam Noy, and Peter J. Roth. "Multicomponent isocyanide-based synthesis of reactive styrenic and (meth)acrylic monomers and their RAFT (co)polymerization." Polymer Chemistry 6, no. 1 (2015): 44–54. http://dx.doi.org/10.1039/c4py01147c.

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A combination of the Passerini reaction and RAFT polymerization is used to produce novel (co)polymers carrying double bond, protected triple bond, protected alcohol, pentafluorophenyl, and diene side group functionality.

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44

Pettignano, Asja, Julien Leguy, Laurent Heux, Bruno Jean, Aurélia Charlot, and Etienne Fleury. "Multifunctionalization of cellulose microfibrils through a cascade pathway entailing the sustainable Passerini multi-component reaction." Green Chemistry 22, no. 20 (2020): 7059–69. http://dx.doi.org/10.1039/d0gc02532a.

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Through a cascade of chemical derivatizations involving the green Passerini three-component reaction (P-3CR), we describe herein the multifunctionnalization of cellulose microfibrils (MFC) previously subjected to a periodate oxidation step.

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45

Zhu, Yu, Wenhai Lin, Xin Wang, Wei Zhang, Li Chen, and Zhigang Xie. "Constructing reduction-sensitive PEGylated NIRF mesoporous silica nanoparticles via a one-pot Passerini reaction for photothermal/chemo-therapy." Chemical Communications 54, no. 84 (2018): 11921–24. http://dx.doi.org/10.1039/c8cc07106c.

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For the first time, we have obtained a multifunctional nanoplatform (MSN-BDP-PEG) containing disulfide bonds, BODIPY 5 and PEG-CHO via a one-pot Passerini reaction for chemotherapy, phototherapy and NIRF imaging.

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46

Butera, Roberto, Annadka Shrinidhi, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, and Alexander Dömling. "Fourfold symmetric MCR's via the tetraisocyanide 1,3-diisocyano-2,2-bis(isocyanomethyl)propane." Chemical Communications 56, no. 73 (2020): 10662–65. http://dx.doi.org/10.1039/d0cc04522e.

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We developed a gram-scale synthesis of the novel tetraisocyanide 1,3-diisocyano-2,2-bis(isocyanomethyl)propane and applied this in unprecedented fourfold Ugi four-component and Passerini three-component reaction achieving unique symmetric structures.

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47

So, Wing Ho, and Jiang Xia. "On-Resin Passerini Reaction toward C-Terminal Photocaged Peptides." Organic Letters 22, no. 1 (December 19, 2019): 214–18. http://dx.doi.org/10.1021/acs.orglett.9b04182.

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48

Abdelraheem, Eman M. M., Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, and Alexander Dömling. "Artificial Macrocycles by Ugi Reaction and Passerini Ring Closure." Journal of Organic Chemistry 81, no. 19 (September 15, 2016): 8789–95. http://dx.doi.org/10.1021/acs.joc.6b01430.

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49

Vlahoviček-Kahlina, Kristina, Josipa Suć Sajko, and Ivanka Jerić. "C-Linked Glycomimetic Libraries Accessed by the Passerini Reaction." International Journal of Molecular Sciences 20, no. 24 (December 10, 2019): 6236. http://dx.doi.org/10.3390/ijms20246236.

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Abstract:

Carbohydrates and their conjugates are the most abundant natural products, with diverse and highly important biological roles. Synthetic glycoconjugates are versatile tools used to probe biological systems and interfere with them. In an endeavor to provide an efficient route to glycomimetics comprising structurally diverse carbohydrate units, we describe herein a robust, stereoselective, multicomponent approach. Isopropylidene-protected carbohydrate-derived aldehydes and ketones were utilized in the Passerini reaction, giving different glycosylated structures in high yields and diastereoselectivities up to 90:10 diastereomeric ratio (d.r). Access to highly valuable building blocks based on α-hydroxy C-glycosyl acids or more complex systems was elaborated by simple post-condensation methodologies.

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Kaicharla, Trinadh, Santhivardhana Reddy Yetra, Tony Roy, and Akkattu T. Biju. "Engaging isatins in solvent-free, sterically congested Passerini reaction." Green Chemistry 15, no. 6 (2013): 1608. http://dx.doi.org/10.1039/c3gc40454d.

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