Efficient Synthesis of Tetrahydropyrimidines and Pyrrolidines by a Multicomponent Reaction of Dialkyl Acetylenedicarboxylates (=Dialkyl But-2-ynedioates), Amines, and Formaldehyde in the Presence of Iodine as a Catalyst

被引：9

作者：

Das, Biswanath ^{[1
]}

Kanth, Boddu Shashi ^{[1
]}

Shinde, Digambar Balaji ^{[1
]}

Kamble, Vinod T. ^{[2
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500607, Andhra Pradesh, India

[2] Marathwada Univ, Organ Chem Res Lab, Sch Chem Sci, Nanded 431606, Maharashtra, India

来源：

HELVETICA CHIMICA ACTA | 2011年 / 94卷 / 11期

关键词：

Pyrimidines; tetrahydro-; Pyrrolidines; Multicomponent reactions; Iodine; Catalysis; PHOSPHONATES;

D O I：

10.1002/hlca.201100185

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Iodine was explored as an efficient catalyst for the synthesis of tetrahydropyrimidines 4 and pyrrolidines 5 by a multicomponent reaction of dialkyl acetylenedicarboxylates (=dialkyl but-2-ynedioates) 1, amines 2, and HCHO 3 at room temperature (Scheme). When the molar ratios of these substrates were 1:2:4 and 1:1:4, tetrahydropyrimidines and pyrrolidines were formed, respectively. The products were obtained in high yields (7385%) within a short period of time (2535 min).

引用

页码：2087 / 2091

页数：5

共 50 条

[11] Convenient construction of polycyclic architectures via multicomponent reaction of amino acids, dialkyl but-2-ynedioates and 2-(o-hydroxyarylidene)-1,3-indanediones
Liu, Xueyan
Sun, Jing
Yan, Chao-Guo
NEW JOURNAL OF CHEMISTRY, 2022, 46 (24) : 11877 - 11882
[12] A Simple and Efficient Metal-Free Synthesis of Tetrasubstituted Pyrroles by Iodine-Catalyzed Four-Component Coupling Reaction of Aldehydes, Amines, Dialkyl Acetylenedicarboxylates, and Nitromethane
Das, Biswanath
Bhunia, Nisith
Lingaiah, Maram
SYNTHESIS-STUTTGART, 2011, (21): : 3471 - 3474
[13] An efficient synthesis of dialkyl 2-(diphenoxyphosphoryl)-3-(alkylthio)succinates from alkylthiols, triphenyl phosphite and dialkyl acetylenedicarboxylates
I. Yavari
R. Hajinasiri
S. Z. Sayyed-Alangi
N. Iravani
Journal of the Iranian Chemical Society, 2009, 6 : 705 - 709
[14] Facile One-pot Synthesis of Substituted Dihydropyrrol-2-ones via Four-component Domino Reaction of Amines, Dialkyl Acetylenedicarboxylates and Formaldehyde
Sajadikhah, Seyed Sajad
Hazeri, Nourallah
Maghsoodlou, Malek Taher
Habibi-Khorassani, Sayyed Mostafa
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2013, 60 (08) : 1003 - 1006
[15] An Efficient Synthesis of Dialkyl 2-(Diphenoxyphosphoryl)-3-(alkylthio)succinates from Alkylthiols, Triphenyl Phosphite and Dialkyl Acetylenedicarboxylates
Yavari, I.
Hajinasiri, R.
Sayyed-Alangi, S. Z.
Iravani, N.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2009, 6 (04) : 705 - 709
[16] Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of hydantoins - A one-pot synthesis of stable ketenimines
Adib, M
Sayahi, MH
Behnam, B
Sheibani, E
MONATSHEFTE FUR CHEMIE, 2006, 137 (02): : 191 - 196
[17] Reaction Between Isocyanides and Dialkyl Acetylenedicarboxylates in the Presence of Hydantoins – A One-pot Synthesis of Stable Ketenimines
Mehdi Adib
Mohammad Hosein Sayahi
Behrooz Behnam
Esmaeil Sheibani
Monatshefte für Chemie / Chemical Monthly, 2006, 137 : 191 - 196
[18] Efficient synthesis of cyclic β-oxophosphoranes by microwave-assisted reaction of cyclic phosphine oxides and dialkyl acetylenedicarboxylates
Keglevich, G
Dudas, E
Sipos, M
Lengyel, D
Ludanyi, K
SYNTHESIS-STUTTGART, 2006, (08): : 1365 - 1369
[19] Stereoselective Synthesis of Dialkyl 2-(Arylsulfonylamino)-3-(dialkoxyphosphoryl) Succinates by Reaction of Trialkyl(aryl) Phosphites, Dialkyl Acetylenedicarboxylates, and Arylsulfonamides
Hassanabadi, Alireza
Mosslemin, Mohammad H.
Anary-Abbasinejad, Mohammad
Khalesi, Hossain
SYNTHETIC COMMUNICATIONS, 2011, 41 (10) : 1529 - 1535
[20] An efficient synthesis of functionalized β-amino- and β-hydrazinoalkylphosphonates by three-component reaction between trialkyl phosphites, dialkyl acetylenedicarboxylates and aromatic amines or hydrazines
Derranji, Akram Ranjbar
Anary-Abbasinejad, Mohammad
Mohammadi, Marziyeh
MOLECULAR DIVERSITY, 2024, 28 (01) : 73 - 83

← 1 2 3 4 5 →