Ugi Reaction Followed by Intramolecular Diels–Alder Reaction and Elimination of HCl: One‐Pot Approach to Arene‐Fused Isoindolinones

Huang, Jianjun; Du, Xiaochen; Hecke, Kristof Van; Eycken, Erik V. Van der; Pereshivko, Olga P.; Peshkov, Vsevolod A.

doi:10.1002/ejoc.201700747

Cited by 22 publications

(10 citation statements)

References 67 publications

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“…4‐Dimethylaminopyridine in water medium was applied to the intermolecular cyclization of acetyl/benzoyl acetanilides and alkynes giving isoindoline‐1,3‐diones 169 (Table 6, entry 11) [242] . Propiolic acids and amines were used as the alkyne and nitrogen source, respectively, in a Ugi reaction followed by the intramolecular Diels‐Alder cyclization and elimination of HCl giving arene‐fused isoindolinones 170 a and 170 b in a one‐pot procedure (Table 6, entry 12) [243] . Intermolecular Alder‐Ene reactions with diynes and functionalized alkenes was developed to obtain substituted isoindolines 171 .…”

Section: Synthesis Of Isoindolinesmentioning

confidence: 99%

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Neto

Zeni

2021

Asian J Org Chem

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This review is intended to highlight the most useful approaches for the synthesis of indole derivatives (azaindoles, carbazoles, carbolines, indazoles, 3H-indoles, indolines, indolizines, isoindoles, and isoindolines), which were described by using transition-metal catalyzed cyclization reactions of alkynes and nitrogen compounds. The methodologies carried out under metal-free conditions will also be illustrated herein. This review will cover the data published mostly in the past decade. Synthesis of 6-AzaindolesAzaindoles, although rare in nature, have attracted a significant attention because some synthetic structures containing this nucleus exhibit biological activities. [17] The synthetic methods describing the preparation of azaindoles are limited. Usually their synthesis was achieved from the cyclization reaction of substrates containing aminopyridines. [18] Transition Metal-Free Synthesis of 6-AzaindolesWe have nominated two methodologies for the preparation of 6-azaindoles, which were developed using alkynes and nitrogen compounds in a metal-free protocol. In the first, an electrophilic cyclization condition, using iodine as an electrophilic source, was applied to 2-(azidomethyl)-3-alkynyl-pyrroles in the preparation of 4-iodo-6-azaindoles 1 (Scheme 1, eq 1). [19] The second approach described the preparation of 2,5-disubstituted 6azaindoles 2 from base-catalyzed intramolecular cyclization of 2-(azidomethyl)-3-alkynyl-pyrroles (Scheme 1, eq 2). [20] 3. Synthesis of 7-Azaindoles Transition Metal-Catalyzed Synthesis of 7-Azaindoles Silver-Catalyzed Synthesis of 7-AzaindolesSilver-catalyzed cyclization reactions of alkynes constitute powerful strategies for the construction of heterocycles. In particular, the 7-azaindoles could be obtained by these approaches. A general method for the preparation of aryl-[a] Dr. J.

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Section: Synthesis Of Isoindolinesmentioning

confidence: 99%

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Neto

Zeni

2021

Asian J Org Chem

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“…Recently, Peshkov et al. developed an efficient Ugi/Diels‐Alder/HCl elimination process for the rapid one‐pot synthesis of complex 2,3‐dihydrobenzo[ f ]isoindolones (Scheme 1c) [9] . Despite the presence of some efficient routes in the literature, the synthetic protocols to 2,3‐dihydrobenzo[ f ]isoindolones are still rare.…”

Section: Figurementioning

confidence: 99%

Regioselective Synthesis of 2,3‐Dihydrobenzo[f]isoindolones via Ag‐Catalyzed Sequential Ugi 4CR/Cascade Radical Cyclization Reaction

Yan

Ren

et al. 2021

Adv Synth Catal

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An approach to 2,3‐dihydrobenzo[f]isoindolones by a Ag‐catalyzed Ugi 4CR/cascade radical cyclization sequence under mild conditions has been developed. The reaction of (E)‐2‐benzylidene‐4‐arylbut‐3‐ynoic acids, aldehydes, amines, and isocyanides produced 2,3‐dihydro‐benzo[f]isoindolones regioselectively in 60–85% yields via sequential Ugi 4CR/cascade radical cyclization reaction in the presence of Cs2CO3 and AgOTf. The method achieved the formation of two C−C bonds under air atmosphere in one‐pot fashion.

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“…During the nonsymmetrical preparation of some compounds from isoindolin-1-one, they can be introduced as building blocks for a Diels-Alder reaction [21][22][23][24][25]. Because of the multibiological properties of isoindoline derivatives, many chemical pathways have been reported for the preparation of these heterocycles [26][27][28][29][30][31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and in vitro bioactivity studies of isoindolin‐1‐3‐phosophonate compounds

Jelali

Nasr

Koko

et al. 2022

Journal of Heterocyclic Chem

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In this work, efficient synthesis of isoindolin-1-one-3-phosphonates under catalyst-and solvent-free conditions was reported to afford the desired compounds in excellent yields with potent pharmacological properties. The synthesis method involves the preparation of isoindolin-1-one-3-phosphonates by a "one-pot" three-component reaction of 2-formylbenzoic acid with primary amines and dimethyl phosphite under solvent-and catalyst-free conditions.All new compounds were characterized by 1 H NMR, 13 C NMR, FT-IR and elemental analysis techniques. The compounds were investigated for their bioactivities against a group of microorganisms, Leishmania major, Toxoplasma gondii parasites, and the DA-MB-231 and MCF-7 cancer cell lines in vitro.Compound 4a was found to be the most active against L. M. luteus, L. monocytogenes and C. albicans microorganisms, with inhibition zones of 35, 22 and 38 mm, respectively. The compounds were also investigated for their antiparasitic activities, and compounds 4a and 4b were the most active against L. major amastigotes and promastigotes with EC 50 < 1 μM. All tested compounds had potent anticancer activity against the MDA-MB-231 and MCF-7 human cell lines with EC 50 < 1.5 μM. Compounds 4a and 4b are good drug candidates for antimicrobial, antileishmanial and anticancer drug discovery, and further in vivo studies are highly recommended prior to any clinical trials.

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Ugi Reaction Followed by Intramolecular Diels–Alder Reaction and Elimination of HCl: One‐Pot Approach to Arene‐Fused Isoindolinones

Cited by 22 publications

References 67 publications

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

Regioselective Synthesis of 2,3‐Dihydrobenzo[f]isoindolones via Ag‐Catalyzed Sequential Ugi 4CR/Cascade Radical Cyclization Reaction

Synthesis, characterization and in vitro bioactivity studies of isoindolin‐1‐3‐phosophonate compounds

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