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

[1] On the Reactivity of N-Substituted Imidates Towards 1,4-Bisnucleophiles: An Experimental and Theoretical Study
Sarra Ouni
Abderrahmen Abdelli
Anne Gaucher
Youssef Arfaoui
Damien Prim
Mohamed Lotfi Efrit
Chemistry Africa, 2022, 5 : 1265 - 1273
[2] Theoretical and experimental study of dimethyl sulfoxide and N-substituted DMSO
Naganathappa, Mahadevappa
Chaudhari, Ajay
INDIAN JOURNAL OF PURE & APPLIED PHYSICS, 2019, 57 (04) : 261 - 267
[3] Reactivity of β-substituted phosphoenol pyruvates towards alkoxides: a theoretical and experimental study
Bassou, Djilali
Ghomri, Amina
Atmani, Abdelkrim
PROGRESS IN REACTION KINETICS AND MECHANISM, 2018, 43 (3-4) : 211 - 218
[4] On the reactivity of 6-acetyl-7-(2-dimethylaminovinyl)pyrazolo[1,5-a]pyrimidines with 1,3- and 1,4-bisnucleophiles
Chimichi, Stefano
Boccalini, Marco
Selleri, Silvia
Costagli, Camilla
Guerrini, Gabriella
Viola, Giampietro
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (04) : 739 - 744
[5] Synthesis of N-substituted amidinoheteroles and their reactivity towards Burgess reagent
Uchiyama, Yosuke
Kimura, Shinobu
Kurotaki, Takanori
Sawamura, Yukihiro
Kikuchi, Yuichi
Abe, Shinya
Runyon, Jason W.
Dolphin, Joshua S.
Schinnen, Christoph
Arduengo, Anthony J., III
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2020, 195 (01) : 3 - 6
[6] N-substituted sumanene and cation-it interactions towards Li cations: A theoretical study
Petrushenko, I. K.
Shipitsin, N. V.
Petrushenko, K. B.
PHYSICA E-LOW-DIMENSIONAL SYSTEMS & NANOSTRUCTURES, 2022, 135
[7] REACTIVITY OF NUCLEOPHILES TOWARDS SOME N-SUBSTITUTED 2-CHLOROBENZIMIDAZOLES
NDIAYE, I
MAYRARGUE, J
COMBETFARNOUX, C
MIOCQUE, M
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1988, (01): : 139 - 142
[8] Experimental and theoretical studies of photophysical properties of N-Substituted iminocoumarins
Jlaiel, Rihab
Elleuch, Slim
Abid, Souhir
Abid, Younes
Ammar, Houcine
OPTICAL MATERIALS, 2022, 134
[9] UNEQUIVOCAL SYNTHESIS OF N-SUBSTITUTED 1,4-DIHYDROPYRIDINES
STOUT, DM
TAKAYA, T
MEYERS, AI
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (05): : 563 - 569
[10] CARDIOVASCULAR EFFECT OF N-SUBSTITUTED 1,4-DIHYDROPYRIDINES
VITOLINYA, RO
KIMENIS, AA
KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1984, 18 (01): : 42 - 43

← 1 2 3 4 5 →