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Journal articles on the topic 'Intramolecular Ugi reaction'

Author: Grafiati

Published: 4 June 2025

Last updated: 1 August 2025

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1

Horak, Yuriy I., Roman Z. Lytvyn, Andrii R. Vakhula, Yuriy V. Homza, Nazariy T. Pokhodylo, and Mykola D. Obushak. "New tandem Ugi/intramolecular Diels–Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives." Beilstein Journal of Organic Chemistry 21 (February 26, 2025): 444–50. https://doi.org/10.3762/bjoc.21.31.

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A new tandem sequence involving the Ugi reaction and Diels–Alder [4 + 2] cycloaddition based on vinylfuran and 1,3-butadienylfuran derivatives was designed and studied. It was found that in the case of 3-(furan-2-yl)acrylaldehyde, a one-pot Ugi reaction and intramolecular Diels–Alder vinylarene (IMDAV) reaction leads to the formation of the insufficiently studied furo[2,3-f]isoindole derivatives. Ugi adducts formed from (E)-3-(furan-2-yl)acrylaldehyde, maleic acid monoanilide, isonitrile, and an amine spontaneously underwent the IMDAV reaction with a high level of stereoselectivity, leading to

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2

Gülten, Ş. "The Ugi Four-Component Reaction: Application in the synthesis of bis-hydantoins." Bulgarian Chemical Communications 56, no. D1 (2024): 13–18. http://dx.doi.org/10.34049/bcc.56.d.s2l4.

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Three new bis 1,3,5-trisubstituted hydantoins were synthesized by combining an Ugi four-component condensation reaction with a base induced cyclization. In the two-step sequence, first three new bis Ugi compounds were synthesized by the Ugi four-component condensation reaction, and then bis 1,3,5-trisubstituted hydantoins were obtained by intramolecular cyclization reaction.

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3

Vroemans, Robby, Fante Bamba, Jonas Winters, et al. "Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins." Beilstein Journal of Organic Chemistry 14 (March 14, 2018): 626–33. http://dx.doi.org/10.3762/bjoc.14.49.

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A practical three-step protocol for the assembly of triazolobenzodiazepine-fused diketopiperazines and hydantoins has been developed. The synthesis of these tetracyclic ring systems was initiated by an Ugi reaction, which brought together all necessary functionalities for further transformations. The Ugi adducts were then subjected to a base-induced ring closing and an intramolecular azide–alkyne cycloaddition reaction in succession to obtain highly fused benzodiazepine frameworks.

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4

Marcaccini, Stefano, Roberto Pepino, Tomás Torroba, Daniel Miguel, and Marı́a Garcı́a-Valverde. "Synthesis of thiomorpholines by an intramolecular Ugi reaction." Tetrahedron Letters 43, no. 47 (2002): 8591–93. http://dx.doi.org/10.1016/s0040-4039(02)02064-6.

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5

Kumar, Amit, Dipak D. Vachhani, Sachin G. Modha, Sunil K. Sharma, Virinder S. Parmar, and Erik V. Van der Eycken. "Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines." Beilstein Journal of Organic Chemistry 9 (October 14, 2013): 2097–102. http://dx.doi.org/10.3762/bjoc.9.246.

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An Ugi four-component reaction of propargylamine with 3-formylindole and various acids and isonitriles produces adducts which are subjected to a cationic gold-catalyzed diastereoselective domino cyclization to furnish diversely substituted spiroindolines. All the reactions run via an exo-dig attack in the hydroarylation step followed by an intramolecular diastereoselective trapping of the imminium ion. The whole sequence is atom economic and the application of a multicomponent reaction assures diversity.

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6

Balalaie, Saeed, Atena Nashta Rahimi, Helya Janatian Ghazvini, Frank Rominger, Hossein Zahedian Tejeneki, and Hamid R. Bijanzadeh. "Ultrasound-Activated Atom-Economical Approach to the Synthesis of Highly Substituted Pyrrolidin-2-ones through a Four-Component Ugi/5-endo-trig Intramolecular Radical Cyclization Reaction." Synlett 31, no. 09 (2020): 871–77. http://dx.doi.org/10.1055/s-0040-1707997.

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An efficient and diversity-oriented access to functionalized pyrrolidin-2-ones through an Ugi reaction of readily available starting materials with a subsequent transformation is described. A two-step reaction sequence of a four-component Ugi reaction and an intramolecular radical-cyclization reaction leads to the chemo- and regioselective formation of a single product with high atom economy and good to high yields. The radicalization of the pseudopeptides generated from the first step by a cavitational mechanism produces the key intermediate for the ultrasound-activated formation of γ-lactams

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7

Balalaie, Saeed, Mohammad Shamakli, Ali Nikbakht, et al. "Direct access to isoxazolino and isoxazolo benzazepines from 2-((hydroxyimino)methyl)benzoic acid via a post-Ugi heteroannulation." Organic & Biomolecular Chemistry 15, no. 27 (2017): 5737–42. http://dx.doi.org/10.1039/c7ob01142c.

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A diversity-oriented access to isoxazolino and isoxazolo benzazepines is elaborated via a post-Ugi heteroannulation involving intramolecular 1,3-dipolar cycloaddition reaction of nitrile oxides with alkenes and alkynes.

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8

Khalesi, Maryam, Azim Ziyaei Halimehjani, and Jürgen Martens. "Synthesis of a novel category of pseudo-peptides using an Ugi three-component reaction of levulinic acid as bifunctional substrate, amines, and amino acid-based isocyanides." Beilstein Journal of Organic Chemistry 15 (April 4, 2019): 852–57. http://dx.doi.org/10.3762/bjoc.15.82.

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The synthesis of a novel category of pseudo-peptides via intramolecular Ugi reaction of levulinic acid (4-oxopentanoic acid), aromatic and aliphatic amines, and amino acid-based isocyanides is reported. Levulinic acid was applied as a bifunctional substrate containing both carbonyl and acid moieties suitable for the Ugi reaction. This article provides a facile and convenient one-pot procedure for the synthesis of peptide-like heterocyclic molecules containing 2-pyrrolidone (γ-lactam), amide and ester functional groups with good to excellent yields.

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9

Alonso, Fernando, Sofía L. Acebedo, Andrea C. Bruttomesso, and Javier A. Ramírez. "Synthesis of 4-azasteroids by an intramolecular Ugi reaction." Steroids 73, no. 12 (2008): 1270–76. http://dx.doi.org/10.1016/j.steroids.2008.06.002.

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10

Ghandi, Mehdi, Nahid Zarezadeh, and Abuzar Taheri. "A three-component, intramolecular Ugi reaction toward unique indoloketopiperazines." Tetrahedron Letters 53, no. 26 (2012): 3353–56. http://dx.doi.org/10.1016/j.tetlet.2012.04.090.

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11

Li, Shi-Qiang, Wei Yan, Liu-Jun He, et al. "One-pot synthesis of natural-product inspired spiroindolines with anti-cancer activities." Organic Chemistry Frontiers 9, no. 3 (2022): 682–86. http://dx.doi.org/10.1039/d1qo01694f.

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A post-Ugi/diastereoselective cascade reaction was developed to construct the spiroindoline scaffold through a 5-exo-dig indole cyclization and the intramolecular trapping of the spiro intermediate forming a quaternary carbon center.

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12

Mijangos, Marco V., and Luis D. Miranda. "Multicomponent access to indolo[3,3a-c]isoquinolin-3,6-diones: formal synthesis of (±)-plicamine." Organic & Biomolecular Chemistry 14, no. 15 (2016): 3677–80. http://dx.doi.org/10.1039/c6ob00231e.

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The complete tetracyclic core structure of plicamine, a novel Amaryllidaceae-type alkaloid, was expeditously prepared by an Ugi four-component condensation reaction, followed by a one-pot sequential phenolic oxidation and intramolecular coupling process.

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13

Li, Jie, Jiu Hong Huang, Jing Ya Wang, Zhi Gang Xu, Zhong Zhu Chen, and Jie Lei. "Correction: An intramolecular hydrogen bond-promoted “green” Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity." RSC Advances 13, no. 8 (2023): 5185. http://dx.doi.org/10.1039/d3ra90013d.

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Correction for ‘An intramolecular hydrogen bond-promoted “green” Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity’ by Jie Li et al., RSC Adv., 2022, 12, 33175–33179, https://doi.org/10.1039/D2RA04958A.

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14

Li, Jie, Jiu Hong Huang, Jing Ya Wang, Zhi Gang Xu, Zhong Zhu Chen, and Jie Lei. "An intramolecular hydrogen bond-promoted “green” Ugi cascade reaction for the synthesis of 2,5-diketopiperazines with anticancer activity." RSC Advances 12, no. 51 (2022): 33175–79. http://dx.doi.org/10.1039/d2ra04958a.

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We report an intramolecular hydrogen bond-promoted Ugi cascade reaction for solvent-free synthesis of 2,5-diketopiperazines. Compounds (±) 5c and (±) 5e displayed potent antitumor activity against acute myeloid leukaemia and prostate cancer cell lines, respectively.

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15

M, Heravi; Majid, and L. Mohammadkhani. "Synthesis of Various N-heterocycles Using the Ugi Four-Center Three-Component Reaction." ChemistrySelect 4, no. 34 (2019): 10187–96. https://doi.org/10.1002/slct.201902029.

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Ugi four-center three-component reaction (U-4 C-3CR) as actually an important development of the well-known Ugi four-component reaction (U-4CR). In U-4 C-3CR, one of the components is bifunctional, reducing the components of U-4CR to three components. This review aims to provide the application of U-4 C-3CR in the synthesis of different N-heterocyclic compounds with four-, five-, six-, and seven-membered rings as well as fused heterocycles.

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16

Golubev, Pavel, Alena Pankova, and Mikhail Krasavin. "“Isocyanide-less” Ugi/Intramolecular Diels-Alder reaction of 5-hydroxymethylfurfural." Tetrahedron Letters 60, no. 24 (2019): 1578–81. http://dx.doi.org/10.1016/j.tetlet.2019.05.018.

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17

Hasan, Muhammad, Anatoly A. Peshkov, Syed Anis Ali Shah, et al. "Silver(I) triflate-catalyzed post-Ugi synthesis of pyrazolodiazepines." Beilstein Journal of Organic Chemistry 21 (May 8, 2025): 915–25. https://doi.org/10.3762/bjoc.21.74.

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A silver(I) triflate-catalyzed post-Ugi assembly of novel pyrazolo[1,5-a][1,4]diazepine scaffolds is reported offering high yields (up to 98%) under mild conditions. The synthetic sequence involves the Ugi four-component reaction (U4CR) of pyrazole-3-carbaldehydes, primary amines, 3-substituted propiolic acids, and isocyanides, followed by a silver(I) triflate-catalyzed intramolecular heteroannulation of the resulting pyrazole-tethered propargylamides occurring in a 7-endo-dig fashion. The approach is scalable and tolerates a diverse range of substitution patterns.

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18

M, Heravi; Majid, M. Shiri, V. Zadsirjan, et al. "Highly regio- and diastereoselective synthesis of oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indoles, based on a post-Ugi condensation: joint experimental and computational study." Journal of the Iranian Chemical Society 16, no. 7 (2019): 1517–26. https://doi.org/10.1007/s13738-019-01632-3.

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A novel series of oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indoles were synthesized via a two-step pathway. In the first step, Ugi-four-component condensation of 2-formylindole, amines, (E)-4-alkoxy-4-oxobut-2-enoic acids, and isocyanides gave the corresponding Ugi-adducts. This adduct underwent intramolecular hydroamination in the presence of K<sub>2</sub>CO<sub>3</sub> in CH<sub>3</sub>CN at room temperature to afford diastereoselective synthesis of a range of oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indoles. A comparison of experimentally observed CD and UV–visible spectra with the theoretica

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19

Torres-Hernández, Fernando, Ángel Rentería-Gómez, and Rocío Gámez-Montaño. "Synthesis of Epoxyisoindolinones via Microwave-Assisted Ugi-4CR/Intramolecular-Diels-Alder Reaction." Cells 3, no. 1 (2020): 83. http://dx.doi.org/10.3390/ecsoc-24-08425.

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A series of epoxyisoindolinones were synthesized by microwave-assisted post-IMCR transformation-based domino strategy via the Ugi-4CR/Intramolecular-Diels-Alder (U-4CR/IMDA) sequence under mild, solvent-, catalyst-free ecofriendly conditions, and orthogonal-bifunctional components. Epoxyisoindolinones are a privileged core of high interest in medicinal chemistry mainly for its anticancer activity in several cell lines.

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20

Du, Xiaochen, Jianjun Huang, Anton A. Nechaev, et al. "Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones." Beilstein Journal of Organic Chemistry 14 (October 4, 2018): 2572–79. http://dx.doi.org/10.3762/bjoc.14.234.

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A series of propargylamides containing an electron-rich benzene ring was prepared through the Ugi reaction of 3,5-dimethoxyaniline with various propiolic acids, aldehydes and isocyanides. Subjecting these adducts to a gold-catalyzed intramolecular alkyne hydroarylation process allowed to efficiently construct the 2-quinolone core bearing a branched substituent on the nitrogen atom.

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21

Dömling, Alexander, Qiang Zheng, and André Boltjes. "An Ugi Reaction/Intramolecular Cyclization/Oxidation Cascade towards Tetrazole-Linked Dibenzoxazepines." Synthesis 53, no. 11 (2021): 1980–88. http://dx.doi.org/10.1055/s-0040-1706642.

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AbstractA series of tetrazole-linked dibenzo[b,f][1,4]oxazepines is synthesized through a short sequence involving an Ugi tetrazole reaction. The intermediate tetrazole undergoes a potassium carbonate mediated SNAr cyclization, followed by oxidation to afford the target tricyclic heterocyclic scaffold. The optimization, scope and limitations of this two-step and efficient methodology are investigated. A 1000-member library of tetrazole-linked dibenzo[b,f][1,4]oxazepines is generated and the physicochemical properties are analyzed. great

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22

Ghandi, Mehdi, Nahid Zarezadeh, and Abuzar Taheri. "ChemInform Abstract: A Three-Component, Intramolecular Ugi Reaction Toward Unique Indoloketopiperazines." ChemInform 43, no. 42 (2012): no. http://dx.doi.org/10.1002/chin.201242175.

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23

Moni, Lisa, Luca Banfi, Andrea Basso, Alice Brambilla, and Renata Riva. "Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization." Beilstein Journal of Organic Chemistry 10 (January 17, 2014): 209–12. http://dx.doi.org/10.3762/bjoc.10.16.

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An operationally simple protocol for the synthesis of 2,3-dihydrobenzo[f][1,4]oxazepin-3-ones, based on an Ugi reaction of an ortho-(benzyloxy)benzylamine, glycolic acid, an isocyanide and an aldehyde, followed by an intramolecular Mitsunobu substitution was developed. The required ortho-(benzyloxy)benzylamines have been in situ generated from the corresponding azides, in turn prepared in high yields from salicylic derivatives.

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24

Li, Yong, Liujun He, Hongxia Qin, et al. "A Facile Ugi/Ullmann Cascade Reaction to Access Fused Indazolo-Quinoxaline Derivatives with Potent Anticancer Activity." Molecules 29, no. 2 (2024): 464. http://dx.doi.org/10.3390/molecules29020464.

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A facile methodology for the construction of a complex heterocycle indazolo-fused quinoxalinone has been developed via an Ugi four-component reaction (U-4CR) followed by an intramolecular Ullmann reaction. The expeditious process features an operationally simple approach, time efficiency, and a broad substrate scope. Biological activity was evaluated and demonstrated that compound 6e inhibits human colon cancer cell HCT116 proliferation with an IC50 of 2.1 μM, suggesting potential applications for developing a drug lead in medicinal chemistry.

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25

Shang, Tianyi, and Yan Liu. "Ugi/Palladium-Catalysed Intramolecular Cyclopropyl Direct Alkenylation Cascade Reaction Providing Access to Azacycles." IOP Conference Series: Materials Science and Engineering 452 (December 12, 2018): 022128. http://dx.doi.org/10.1088/1757-899x/452/2/022128.

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26

Mazur, Maryna O., Oleksii S. Zhelavskyi, Eugene M. Zviagin, et al. "Effective microwave-assisted approach to 1,2,3-triazolobenzodiazepinones via tandem Ugi reaction/catalyst-free intramolecular azide–alkyne cycloaddition." Beilstein Journal of Organic Chemistry 17 (March 8, 2021): 678–87. http://dx.doi.org/10.3762/bjoc.17.57.

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A novel catalyst-free synthetic approach to 1,2,3-triazolobenzodiazepinones has been developed and optimized. The Ugi reaction of 2-azidobenzaldehyde, various amines, isocyanides, and acids followed by microwave-assisted intramolecular azide–alkyne cycloaddition (IAAC) gave a series of target heterocyclic compounds in moderate to excellent yields. Surprisingly, the normally required ruthenium-based catalysts were found to not affect the IAAC, only making isolation of the target compounds harder while the microwave-assisted catalyst-free conditions were effective for both terminal and non-termi

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27

Balalaie, Saeed, Aref Vaezghaemi, Nahid Zarezadeh, Frank Rominger, and Hamid Bijanzadeh. "Catalyst-Free Synthesis of Fused Triazolo-Diazepino[5,6-b]Quinoline Derivatives via a Sequential Ugi-4CR–Nucleophilic Substitution–Intramolecular Click Reaction." Synlett 29, no. 08 (2018): 1095–101. http://dx.doi.org/10.1055/s-0036-1591531.

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A convenient, post-transformational reaction has been developed for the construction of highly diversified quinoline-fused triazolo-diazepinones featuring four diversification points by employing a catalyst-free Ugi four-component–nucleophilic substitution–intramolecular click cycloaddition sequence. This approach provides a wide scope of products with good yields and high bond-forming efficiency.

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28

Vázquez-Vera, Óscar, Daniel Segura-Olvera, Mónica Rincón-Guevara, et al. "Synthesis of New 5-Aryl-benzo[f][1,7]naphthyridines via a Cascade Process (Ugi-3CR/Intramolecular Aza-Diels-Alder Cycloaddition)/Aromatization." Molecules 23, no. 8 (2018): 2029. http://dx.doi.org/10.3390/molecules23082029.

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A series of eight new 5-aryl-benzo[f][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugi–three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophile-containing ester-anilines, substituted benzaldehydes and the chain-ring tautomerizable 2-isocyano-1-morpholino-3-phenylpropan-1-one as starting reagents, under mild conditions. The doubly activated dienophile and the aza-diene functionalities of the eight new Ugi-adducts were exploited to perform

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29

Xu, Jia, Yong Li, Jiang-Ping Meng, et al. "Efficient microwave-assisted synthesis of fused benzoxazepine–isoquinoline derivatives via an Ugi reaction/tautomerization/intramolecular SNAr reaction sequence." Tetrahedron Letters 58, no. 16 (2017): 1640–43. http://dx.doi.org/10.1016/j.tetlet.2017.03.036.

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30

Trifilenkov, Andrey S., Alexey P. Ilyin, Volodymyr M. Kysil, Yuri B. Sandulenko, and Alexandre V. Ivachtchenko. "One-pot tandem complexity-generating reaction based on Ugi four component condensation and intramolecular cyclization." Tetrahedron Letters 48, no. 14 (2007): 2563–67. http://dx.doi.org/10.1016/j.tetlet.2007.02.015.

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31

Huang, Jianjun, Xiaochen Du, Kristof Van Hecke, Erik V. Van der Eycken, Olga P. Pereshivko, and Vsevolod A. Peshkov. "Ugi Reaction Followed by Intramolecular Diels-Alder Reaction and Elimination of HCl: One-Pot Approach to Arene-Fused Isoindolinones." European Journal of Organic Chemistry 2017, no. 30 (2017): 4379–88. http://dx.doi.org/10.1002/ejoc.201700747.

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32

Singh Chouhan, Pradeep, Deepti Singh, Pooja Purohit, et al. "PPh 3 Catalyzed Post‐Transformation Ugi‐4CR Intramolecular Cyclization Reaction: One‐Pot Synthesis of Functionalized Spiropyrrolidinochromanones." ChemistrySelect 6, no. 6 (2021): 1216–22. http://dx.doi.org/10.1002/slct.202003936.

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33

Ilyin, Alexei, Volodymyr Kysil, Mikhail Krasavin, Irina Kurashvili, and Alexandre V. Ivachtchenko. "Complexity-Enhancing Acid-Promoted Rearrangement of Tricyclic Products of Tandem Ugi 4CC/Intramolecular Diels−Alder Reaction." Journal of Organic Chemistry 71, no. 25 (2006): 9544–47. http://dx.doi.org/10.1021/jo061825f.

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34

Harriman, Geraldine C. B. "Synthesis of small and medium sized 2,2-disubstituted lactams via the “intramolecular” three component Ugi reaction." Tetrahedron Letters 38, no. 32 (1997): 5591–94. http://dx.doi.org/10.1016/s0040-4039(97)01265-3.

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35

Nayl, AbdElAziz A., Ashraf A. Aly, Wael A. A. Arafa, et al. "Azides in the Synthesis of Various Heterocycles." Molecules 27, no. 12 (2022): 3716. http://dx.doi.org/10.3390/molecules27123716.

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In this review, we focus on some interesting and recent examples of various applications of organic azides such as their intermolecular or intramolecular, under thermal, catalyzed, or noncatalyzed reaction conditions. The aforementioned reactions in the aim to prepare basic five-, six-, organometallic heterocyclic-membered systems and/or their fused analogs. This review article also provides a report on the developed methods describing the synthesis of various heterocycles from organic azides, especially those reported in recent papers (till 2020). At the outset, this review groups the synthet

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36

Morteza, Shiri, Zadsirjan Vahideh, A. Koorbanally Neil, A. Shintre Suhas, Hosseinnejad Tayebeh, and M. Heravi Majid. "Molecular diversity in cyclization of Ugi-products leading to the synthesis of 2,5-diketopiperazines: computational study." Research on Chemical Intermediates 43, no. 4 (2016): 2119–42. https://doi.org/10.1007/s11164-016-2750-1.

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Ugi-adducts were obtained via a one-pot four-component reaction of divergent aldehydes, amines, aroylacrylic acids and isocyanide in methanol. These products were subjected to intramolecular Michael addition in the presence of K2CO3 in DMF at room temperature to afford a single product. Literally, the formation of two heterocyclic systems, 6membered diones or 7-membered diones are possible, which could not be identified by conventional spectroscopic methods. The X-ray crystallographical data was obtained for one selected product, which indicated preferential formation of the corresponding 6mem

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37

Foley, Christopher, Arthur Shaw, and Christopher Hulme. "Two-Step Route to DiverseN-Functionalized Peptidomimetic-like Isatins through an Oxidation/Intramolecular Oxidative-Amidation Cascade of Ugi Azide and Ugi Three-Component Reaction Products." Organic Letters 18, no. 19 (2016): 4904–7. http://dx.doi.org/10.1021/acs.orglett.6b02383.

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38

Cristau, Pierre, Jean-Pierre Vors, and Jieping Zhu. "Rapid Synthesis of Cyclopeptide Alkaloid-Likepara-Cyclophanes by Combined Use of Ugi-4CR and Intramolecular SNAr Reaction." QSAR & Combinatorial Science 25, no. 5-6 (2006): 519–26. http://dx.doi.org/10.1002/qsar.200540214.

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39

HARRIMAN, G. C. B. "ChemInform Abstract: Synthesis of Small and Medium Sized 2,2-Disubstituted Lactams via the “ Intramolecular” Three Component Ugi Reaction." ChemInform 28, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199745120.

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40

Gambuti, Francesco, Jacopo Pizzorno, Chiara Lambruschini, Renata Riva, and Lisa Moni. "Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light." Beilstein Journal of Organic Chemistry 20 (October 29, 2024): 2722–31. http://dx.doi.org/10.3762/bjoc.20.230.

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Spiro-heterocyclic indolenines are privileged scaffolds widely present in numerous indole alkaloids. Here, we develop a novel approach for the one-pot multistep synthesis of different spiro[indole-isoquinolines]. The protocol proposed involves the visible light mediated oxidation of N-aryl tertiary amines using bromochloroform with the generation of a reactive iminium species, which reacts with an isocyanide and an electron-rich aniline in a three-component Ugi-type reaction to give an α-aminoamidine. This compound might undergo an additional visible light-mediated oxidation to furnish a secon

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41

Bay, Sarah, Gamall Makhloufi, Christoph Janiak, and Thomas J. J. Müller. "The Ugi four-component reaction as a concise modular synthetic tool for photo-induced electron transfer donor-anthraquinone dyads." Beilstein Journal of Organic Chemistry 10 (May 5, 2014): 1006–16. http://dx.doi.org/10.3762/bjoc.10.100.

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Phenothiazinyl and carbazolyl-donor moieties can be covalently coupled to an anthraquinone acceptor unit through an Ugi four-component reaction in a rapid, highly convergent fashion and with moderate to good yields. These novel donor–acceptor dyads are electronically decoupled in the electronic ground state according to UV–vis spectroscopy and cyclic voltammetry. However, in the excited state the inherent donor luminescence is efficiently quenched. Previously performed femtosecond spectroscopic measurements account for a rapid exergonic depopulation of the excited singlet states into a charge-

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Bonnaterre, Florence, Michèle Bois-Choussy, and Jieping Zhu. "Rapid Access to Oxindoles by the Combined Use of an Ugi Four-Component Reaction and a Microwave-Assisted Intramolecular Buchwald−Hartwig Amidation Reaction." Organic Letters 8, no. 19 (2006): 4351–54. http://dx.doi.org/10.1021/ol061755z.

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Shang, Tianyi, Yan Pan, Zhong Chen, et al. "Solvent-Controlled Cascade Reaction of Ugi/Pd-Catalyzed Intramolecular Divergent C-H Functionalization for Regioselective Synthesis of Cyclopropanated N-Heterocycles." IOP Conference Series: Materials Science and Engineering 612 (October 19, 2019): 022108. http://dx.doi.org/10.1088/1757-899x/612/2/022108.

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Paulvannan, K. "An Atom-Economical Approach to Conformationally Constrained Tricyclic Nitrogen Heterocycles via Sequential and Tandem Ugi/Intramolecular Diels−Alder Reaction of Pyrrole1,2." Journal of Organic Chemistry 69, no. 4 (2004): 1207–14. http://dx.doi.org/10.1021/jo030231z.

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Gülten, Şirin. "Synthesis of Fused Six-Membered Lactams to Isoxazole and Isoxazoline by Sequential Ugi Four-Component Reaction and Intramolecular Nitrile Oxide Cyclization." Journal of Chemical Education 97, no. 10 (2020): 3839–46. http://dx.doi.org/10.1021/acs.jchemed.9b01169.

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Yan, Yan-Mei, Meng-Liang Wang, Yu-Long Liu та Ying-Chun He. "One-pot and regioselective synthesis of functionalized γ-lactams via a metal-free sequential Ugi 4CR/Intramolecular 5-exo-dig cyclization reaction". Tetrahedron 76, № 34 (2020): 131389. http://dx.doi.org/10.1016/j.tet.2020.131389.

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Basso, Andrea, Luca Banfi, Giuseppe Guanti, and Renata Riva. "A novel intramolecular Ugi reaction with 7-azabicyclo[2.2.1]heptane derivatives followed by post-condensation acylations: a new entry to azanorbornyl peptidomimetics." Org. Biomol. Chem. 7, no. 2 (2009): 253–58. http://dx.doi.org/10.1039/b812304g.

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Banfi, Luca, Andrea Basso, Giuseppe Guanti, Nicola Kielland, Claudio Repetto, and Renata Riva. "Ugi Multicomponent Reaction Followed by an Intramolecular Nucleophilic Substitution: Convergent Multicomponent Synthesis of 1-Sulfonyl 1,4-Diazepan-5-ones and of Their Benzo-Fused Derivatives." Journal of Organic Chemistry 72, no. 6 (2007): 2151–60. http://dx.doi.org/10.1021/jo062626z.

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Giustiniano, Mariateresa, Lisa Moni, Gian Tron, et al. "Interrupted Ugi and Passerini Reactions: An Underexplored Treasure Island." Synthesis 50, no. 18 (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 o

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Ackermann, Stefanie, Hans-Georg Lerchen, Dieter Häbich, Angelika Ullrich, and Uli Kazmaier. "Synthetic studies towards bottromycin." Beilstein Journal of Organic Chemistry 8 (October 1, 2012): 1652–56. http://dx.doi.org/10.3762/bjoc.8.189.

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Thio-Ugi reactions are described as an excellent synthetic tool for the synthesis of sterically highly hindered endothiopeptides. S-Methylation and subsequent amidine formation can be carried out in an inter- as well as in an intramolecular fashion. The intramolecular approach allows the synthesis of the bottromycin ring system in a straightforward manner.

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