Synthesis of bridgehead-azacycles <i>via</i> dual C–N/C–C annulation of α-amino acids, aminals and maleimides

Thadem, Nagender; Rajesh, Manda; Balaboina, Harikrishna; Das, Saibal

doi:10.1039/d2ob01117d

Cited by 4 publications

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References 71 publications

(66 reference statements)

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“…The easily available and flexible reactive maleimides have recently attracted a great amount of attention from synthetic organic chemists, because of the omnipresent nature of these motifs in various fields of biology . Especially, the succinimide and its fused derivatives are frequently present in natural products and biologically intriguing molecules (see Figure ).…”

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Acylsilane Directed Rh-Catalyzed Arene C–H Alkylation with Maleimides and Visible-Light-Induced Siloxycarbene-Amide Cyclization: [3 + 2] Carbo-Annulation in Ru Catalysis

et al. 2023

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We herein demonstrate the acylsilane-directed Rh-catalyzed arene C−H bond alkylation with maleimides. The resulting derivatives were utilized in visible-light-induced intramolecular siloxycarbene-amide cyclization for the synthesis of new tricyclic γ-lactams. In parallel, we also harnessed the same acylsilane and maleimide units through [3 + 2] carbo-annulation by using Ru-catalysis. A wide range of maleimides and aroylsilanes were used to establish the broadness of these transformations.

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confidence: 99%

Acylsilane Directed Rh-Catalyzed Arene C–H Alkylation with Maleimides and Visible-Light-Induced Siloxycarbene-Amide Cyclization: [3 + 2] Carbo-Annulation in Ru Catalysis

et al. 2023

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Chemoselective Oxypalladation of (o‐Alkynylaryl)amide‐Triggered Site‐Selective C−H Annulation for Stereoselective Synthesis of Succinimide‐Fused Polycycles

Dattatri,

Babu Nanubolu,

Sridhar Reddy

2024

Adv Synth Catal

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We report herein a palladium‐catalyzed, site‐selective cyclative annulation of o‐alkynyl arylamides with maleimide for the stereoselective construction of succinimide‐incorporated benzoxazine derivatives. This operationally simple and modular protocol provides access to polycyclic frameworks. The other associated features are high functional group compatibility, gram‐scale synthetic potential, and downstream transformations. Control and labeling experiments were conducted to get insights into the mechanism.

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Seven-membered rings

Hawkins,

Bissember,

Wales

et al. 2023

Progress in Heterocyclic Chemistry

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Synthesis of bridgehead-azacycles via dual C–N/C–C annulation of α-amino acids, aminals and maleimides

Abstract: The synthesis of various bridged azocyclic adducts is a reemergence topic in recent past due to their bioactive and natural product mimic profiles. To this point, we herein report an...

Cited by 4 publications

References 71 publications

Acylsilane Directed Rh-Catalyzed Arene C–H Alkylation with Maleimides and Visible-Light-Induced Siloxycarbene-Amide Cyclization: [3 + 2] Carbo-Annulation in Ru Catalysis

Acylsilane Directed Rh-Catalyzed Arene C–H Alkylation with Maleimides and Visible-Light-Induced Siloxycarbene-Amide Cyclization: [3 + 2] Carbo-Annulation in Ru Catalysis

Chemoselective Oxypalladation of (o‐Alkynylaryl)amide‐Triggered Site‐Selective C−H Annulation for Stereoselective Synthesis of Succinimide‐Fused Polycycles

Seven-membered rings

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