Ring Expansion Reactions through Intramolecular Transamidation

被引:5
作者
Kalinin, Stanislav [1 ]
Sapegin, Alexander [1 ]
机构
[1] St Petersburg State Univ, Inst Chem, 26 Universitetskii Prospect, St Petersburg 198504, Russia
基金
俄罗斯科学基金会;
关键词
aminoacyl inclusion; intramolecular transamidation; lactams; medium-sized cycles; ring expansion; ZIP REACTION; REAMIDATION REACTIONS; BETA-LACTAMS; ENLARGEMENT; HETEROCYCLES;
D O I
10.1002/ejoc.202300754
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthetic methodologies based on cycle expansion reactions have proven to be highly effective in delivering valuable medium-sized cycles and macrocycles. A primary method of ring expansion relies on intramolecular transamidation reactions. These reactions typically employ N-aminoalkyl and N-aminoacyl derivatives of lactams and their analogues as starting materials, yielding a diverse spectrum of unique nitrogen-containing heterocycles.This Review aims to provide a comprehensive analysis of the research outcomes related to intramolecular transamidation reactions that lead to cycle expansion. This will offer the reader a perspective on the potential applications of such reactions in generating novel and intriguing types of heterocyclic systems. This review summarizes examples of ring expansion reactions through intramolecular transamidation. This synthetic approach allows the preparation of a wide range of nitrogen-containing heterocycles.image
引用
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页数:11
相关论文
共 58 条
[1]   Chemoselective Ru-Catalyzed Oxidative Lactamization vs Hydroamination of Alkynylamines: Insights from Experimental and Density Functional Theory Studies [J].
Alvarez-Constantino, Andres M. ;
Alvarez-Perez, Andrea ;
Varela, Jesus A. ;
Sciortino, Giuseppe ;
Ujaque, Gregori ;
Saa, Carlos .
JOURNAL OF ORGANIC CHEMISTRY, 2022, 88 (02) :1185-1193
[2]  
ANTONOV VK, 1964, TETRAHEDRON LETT, P727
[3]   TRANSFORMATION OF SACCHARIN INTO DERIVATIVES OF "IMIDAZO[1,2-B][1,2]-BENZISOTHIAZOLE AND BENZO[G][1,2,5]THIADIAZOCINE [J].
ASHBY, J ;
GRIFFITHS, D ;
PATON, D .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1978, 15 (06) :1009-1020
[4]   At the Crossroads of Heterocyclic and Peptide Chemistries. The Aminoacyl Incorporation Reaction in the Synthesis of Medium-Sized Ring Heterocycles (Review) [J].
Azev, V. N. ;
Chulin, A. N. ;
Rodionov, I. L. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 50 (02) :145-159
[5]   Intramolecular opening of β-lactams with amines as a strategy toward enzymatically or photochemically triggered activation of lactenediyne prodrugs [J].
Banfi, L ;
Guanti, G ;
Rasparini, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (07) :1319-1336
[6]   Intramolecular transamidation of β-lactams as a means for the enzymatic control of ring opening:: Effect of substituents on the rate of reaction [J].
Banfi, L ;
Guanti, G ;
Rasparini, M .
TETRAHEDRON LETTERS, 1998, 39 (51) :9539-9542
[7]   SYNTHESES OF THE SPERMIDINE ALKALOIDS (+/-)-INANDENIN-10-OL, INANDENIN-10-ONE, AND (+/-)-ONCINOTINE [J].
BIENZ, S ;
GUGGISBERG, A ;
WALCHLI, R ;
HESSE, M .
HELVETICA CHIMICA ACTA, 1988, 71 (07) :1708-1718
[8]  
Calcagni A., 2009, Int. J. Pept. Protein Res, V42, P84
[9]  
Calcagni A., 2009, Int. J. Pept. Protein Res, V34, P471
[10]  
Cerrini S., 2009, Int. J. Pept. Protein Res, V38, P289