On the Reactivity of N-Substituted Imidates Towards 1,4-Bisnucleophiles: An Experimental and Theoretical Study

被引：0

作者：

Ouni, Sarra ^{[1
,2
]}

Abdelli, Abderrahmen ^{[1
]}

Gaucher, Anne ^{[2
]}

Arfaoui, Youssef ^{[3
]}

Prim, Damien ^{[2
]}

Efrit, Mohamed Lotfi ^{[1
]}

机构：

[1] Univ Tunis El Manar, Fac Sci Tunis, Lab Synth Organ & Heterocycl Select Evaluat Dacti, Campus Univ, Tunis 2092, Tunisia

[2] Univ Paris Saclay, Inst Lavoisier Versailles, CNRS, UVSQ, F-78035 Versailles, France

[3] Univ Tunis El Manar, Fac Sci, Dept Chim, Lab Caracterisat Applicat & Modelisat Mat LR18ES0, Tunis 2092, Tunisia

来源：

CHEMISTRY AFRICA-A JOURNAL OF THE TUNISIAN CHEMICAL SOCIETY | 2022年 / 5卷 / 05期

关键词：

Imidates; 1,4-Binucleophiles; Heterocycles; DFT; CATALYZED SYNTHESIS; CASCADE SYNTHESIS; BENZIMIDAZOLES; QUINAZOLINES; ALKOXYAMIDE; HALIDES; COPPER;

D O I：

10.1007/s42250-022-00452-y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This paper sets out to describe the reaction of N-acyl and N-ethoxycarbonyl imidates with 1,4-bisnucleophiles. The reaction selectively led to 5-membered heterocycles in good yields instead of expected 7-membered ring systems. Using mild reaction conditions, we synthesized 2-imidazoline, benzimidazolines, 2-oxazoline, 2-thiazoline and 2-dithiolane derivatives. Experimental results are supported by theoretical DFT calculations. Our approach has been further extended to 1,5 bis amines towards tetrahydropyrimidine scaffolds. [GRAPHICS] .

引用

页码：1265 / 1273

页数：9

共 50 条

[11] Preparation of the N-substituted 1,4-phthalazinedione derivatives
Baloniak, S
Mroczkiewicz, A
Katrusiak, A
POLISH JOURNAL OF CHEMISTRY, 1996, 70 (10) : 1274 - 1278
[12] Reactivity of hydroxo palladium and platinum complexes towards N-substituted salicylaldimines and β-ketoimines
Jose´ Ruiz
Venancio Rodri´guez
Consuelo Vicente
Gregorio Lo´pez
Transition Metal Chemistry, 1997, 22 : 502 - 506
[13] N-SUBSTITUTED 1,4-DIHYDROQUINA-ZOLIN-4-ONES
SOMASEKHARA, S
SHAH, GM
MUKHERJE, SL
CURRENT SCIENCE, 1964, 33 (17): : 521 - &
[14] A new synthetic approach to N-substituted 1,4-dihydropyridines
De Lucas, AI
Fernández-Gadea, J
Martín, N
Seoane, C
TETRAHEDRON, 2001, 57 (26) : 5591 - 5595
[15] A THEORETICAL-STUDY OF PROTONATION AND TAUTOMERIZATION OF N-SUBSTITUTED AMINOAZOBENZENES
LIWO, A
TEMPCZYK, A
WIDERNIK, T
KLENTAK, T
CZERMINSKI, J
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (01): : 71 - 75
[16] EXPERIMENTAL AND THEORETICAL-STUDIES ON DIAMAGNETIC SUSCEPTIBILITY OF AMIDES AND THEIR N-SUBSTITUTED DERIVATIVES
GUPTA, RR
KUMAR, M
KUMAR, R
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) : 1888 - 1890
[17] SYNTHESIS OF N-SUBSTITUTED PYRROLO[1,2-a][1,4] BENZODIAZEPINES
Stroganova, T. A.
Malikov, I. V.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (09) : 1149 - 1150
[18] Synthesis of N-substituted pyrrolo[1,2-a][1,4]benzodiazepines
T. A. Stroganova
I. V. Malikov
Chemistry of Heterocyclic Compounds, 2009, 45 : 1149 - 1150
[19] Synthesis and crystal structure of a novel n-substituted 1,4-dihydropyridine
Naveen, S.
Anandalwar, Sridhar M.
Prasad, J. Shashidhara
Kakadiya, Rajesh
Bariwal, Jitender
Virsodia, Vijay
Karia, Denish
Shah, Anamik
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2007, 474 : 55 - 65
[20] Synthesis and structural conformation of N-substituted 1,4-dihyropyridine derivatives
Mahendra, M
Doreswamy, BH
Sridhar, MA
Prasad, JS
Parecha, AR
Patel, JA
Manvar, D
Dholaria, K
Shah, A
CRYSTAL RESEARCH AND TECHNOLOGY, 2006, 41 (01) : 92 - 97

← 1 2 3 4 5 →