C-C Bond Cleavage of α-Pyridinium Amides: A Synthetic Approach to Hydantoin Structures

被引：1

作者：

Takallou, Ahmad ^{[1
]}

Sakhaee, Nader ^{[2
]}

Nosood, Yazdanbakhsh Lotfi ^{[1
]}

Al-Shidhani, Sulaiman ^{[1
]}

Al-Siyabi, Munir ^{[1
]}

Mobaraki, Akbar ^{[3
]}

Anwar, Muhammad U. ^{[1
]}

Al-Harrasi, Ahmed ^{[1
]}

机构：

[1] Univ Nizwa, Nat & Med Sci Res Ctr, POB 33, Nizwa 616, Oman

[2] Univ Illinois, Sch Chem Sci, Roger Adams Lab, Champaign, IL 61801 USA

[3] Kharazmi Univ, Fac Chem, Dept Organ Chem & Polymer, Tehran 1571914911, Iran

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 15期

关键词：

Amide; Carbon-Carbon bond Cleavage; Peptides; Bifunctional Structures; Pyridinium Salt; KETONES; ACTIVATION; ALDEHYDES; CATALYST; FACILE; ACIDS;

D O I：

10.1002/adsc.202300653

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

This study reports a mild reaction-condition approach for the direct C-C bond cleavage of amides to form hydantoin structures in the presence of 4-methylpyridine and a base. This approach presents an amide C-C bond cleavage strategy enabling nucleophilic addition to the amide carbonyl involving a reactive spiro intermediate. A broad spectrum of pseudo peptide Ugi adducts as bifunctional starting materials was synthesized and used in this transformation. The mechanistic pathway of this reaction was investigated using experimental and theoretical studies.

引用

页码：2607 / 2614

页数：8

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