TMSOTf-Promoted Cyclization of Indole-2-methyl-α-aminoketones: Access to 4-Aryl-Substituted β-Carbolines

Yang, Xin-Yu; Yang, Jin-Ming; Wu, Bin

doi:10.1021/acs.orglett.3c04382

Org. Lett.

2024

DOI: 10.1021/acs.orglett.3c04382

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TMSOTf-Promoted Cyclization of Indole-2-methyl-α-aminoketones: Access to 4-Aryl-Substituted β-Carbolines

Xin-Yu Yang,

Jin-Ming Yang,

Bin Wu

Abstract: An efficient method to construct 4-aryl-substituted β-carbolines from indole-2-methyl-α-aminoketones via a TMSOTfpromoted annulation reaction was reported. High yield along with wide substrate scope and functional group tolerance make this reaction applicable to build various highly potential bioactive βcarboline derivatives.

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Cited by 3 publications

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Diastereoselective Synthesis of High Functionalized 4‐Imidazolidinone‐Tetrahydro‐β‐Carboline Hybrids via Divergent Post‐Ugi Transformation

Morlacci,

Arcadi,

Aschi

et al. 2024

Adv Synth Catal

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An easily scalable and highly diastereoselective synthesis of challenging 1,2,5,6,11,11b‐hexahydro‐3H‐imidazo[1',2':1,2]pyrido[3,4‐b]indol‐3‐ones is accomplished through divergent transformation of Ugi 4‐CR products. The trimethylsilyl trifluoromethanesulfonate (TMSOTf) mediated intramolecular condensation of a series of Ugi 4‐CR adducts generates a N‐acylimidinium intermediate which undergoes ring closure to selectively afford the target title compounds in good to high yields.

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Diastereoselective Synthesis of High Functionalized 4‐Imidazolidinone‐Tetrahydro‐β‐Carboline Hybrids via Divergent Post‐Ugi Transformation

Morlacci,

Arcadi,

Aschi

et al. 2024

Adv Synth Catal

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One-Pot Total Synthesis of Natural Products Nitramarine, Nitraridine, and Analogues via a Cascade Oxidation/Pictet–Spengler Condensation/Annulation Process

Song,

Cao,

Wang

et al. 2024

J. Org. Chem.

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A cascade oxidation/Pictet–Spengler condensation/annulation process has been developed for the one-pot total synthesis of nitramarine, nitraridine, and their analogues. The procedure proceeded with easily available quinolines and tryptophan derivatives. A simple and metal-free approach, wide substrate scope, and functional group tolerance make it applicable for the synthesis of diverse bioactive nitramarine, nitraridine, and their derivatives. Furthermore, the bioactivity evaluation has identified two promising leading compounds 5d and 5e with potent antitumor proliferative activity against breast cancer cells.

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Access to Piperazine-Fused Pyrrolocarbazoles Enabled by Acid-Catalyzed Stereoselective Hydroarylation of Ynamide–Indoles and Subsequent Diels–Alder Reactions/Aromatizations

Zhou,

Huang,

Wei

et al. 2024

Org. Lett.

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Pyrrolocarbazole skeletons are well known to possess a variety of biological activities that might be therapeutically useful in the treatment of cancers. Herein, an acid-catalyzed stereoselective hydroarylation/Diels–Alder cycloaddition/aromatization of ynamide–indoles is described. We newly designed and synthesized a variety of piperazine-fused pyrrolocarbazole derivatives that could be further applied to the synthesis of potent Wee1 inhibitors.

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TMSOTf-Promoted Cyclization of Indole-2-methyl-α-aminoketones: Access to 4-Aryl-Substituted β-Carbolines

Cited by 3 publications

References 22 publications

Diastereoselective Synthesis of High Functionalized 4‐Imidazolidinone‐Tetrahydro‐β‐Carboline Hybrids via Divergent Post‐Ugi Transformation

Diastereoselective Synthesis of High Functionalized 4‐Imidazolidinone‐Tetrahydro‐β‐Carboline Hybrids via Divergent Post‐Ugi Transformation

One-Pot Total Synthesis of Natural Products Nitramarine, Nitraridine, and Analogues via a Cascade Oxidation/Pictet–Spengler Condensation/Annulation Process

Access to Piperazine-Fused Pyrrolocarbazoles Enabled by Acid-Catalyzed Stereoselective Hydroarylation of Ynamide–Indoles and Subsequent Diels–Alder Reactions/Aromatizations

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