An efficient synthesis of 4H-chromene, 4H-pyran, and oxepine derivatives via one-pot three-component tandem reactions

被引：50

作者：

Kazemi, Bagher ^{[1
]}

Javanshir, Shahrzad ^{[1
]}

Maleki, Ali ^{[1
]}

Safari, Mostafa ^{[1
]}

Khavasi, Hamid Reza ^{[2
]}

机构：

[1] Iran Univ Sci & Technol, Dept Chem, Tehran 1684613114, Iran

[2] Shahid Beheshti Univ, Dept Chem, Tehran 1983953113, Iran

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 51期

关键词：

Oxepine; Pyran; Chromene; Multicomponent reaction; Dialkyl acetylenedicarboxylate; Malononitrile; ISOCYANIDES; SCAFFOLD; ETHERS;

D O I：

10.1016/j.tetlet.2012.10.046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and efficient method has been developed for the synthesis of highly functionalized 2-amino-4H-pyran, 2-amino-4H-chromene, 2-amino-oxepine, and 2-hydroxy-oxepine derivatives through one-pot, three-component tandem reactions of structurally diverse 1,3-diketones, dialkyl acetylenedi-carboxylates, and malononitrile or ethyl cyanoacetate in the presence of a catalytic amount of Na2CO3 in ethanol. This efficient technique has the advantages of giving products in good to high yields, in short reaction times, and with a simple isolation procedure. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：6977 / 6981

页数：5

共 50 条

[1] An Efficient Synthesis of 4H-chromene Derivatives by a One-pot, Three-component Reaction
Poursattar Marjani, Ahmad
Ebrahimi Saatluo, Bahman
Nouri, Fariba
IRANIAN JOURNAL OF CHEMISTRY & CHEMICAL ENGINEERING-INTERNATIONAL ENGLISH EDITION, 2018, 37 (01): : 149 - 157
[2] Biocatalytic one-pot three-component synthesis of 4H-chromene derivatives in non-aqueous medium
Shrivas, Prabhakar
Pratap, Umesh
CHEMICAL PAPERS, 2019, 73 (05): : 1301 - 1307
[3] Biocatalytic one-pot three-component synthesis of 4H-chromene derivatives in non-aqueous medium
Prabhakar Shrivas
Umesh Pratap
Chemical Papers, 2019, 73 : 1301 - 1307
[4] Efficient Synthesis of 4-Phenyl-4H-pyran Derivatives via a DIPEA-catalyzed One-Pot Three-Component Reaction
Jun Li
Jie Li
Shi-yu Hu
Ye Chen
Ju Liu
Russian Journal of Organic Chemistry, 2019, 55 : 1791 - 1799
[5] Efficient Synthesis of 4-Phenyl-4H-pyran Derivatives via a DIPEA-catalyzed One-Pot Three-Component Reaction
Li, Jun
Li, Jie
Hu, Shi-yu
Chen, Ye
Liu, Ju
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (11) : 1791 - 1799
[6] Natural Deep Eutectic Solvent as a Green Catalyst for the One-pot Synthesis of Chromene and 4H-Pyran Derivatives
Valipour, Zohreh
Hosseinzadeh, Rahman
Sarrafi, Yaghoub
Maleki, Behrooz
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2024, 56 (02) : 105 - 117
[7] One-pot, three-component, selective synthesis of the polyfunctionalized 4H-pyran and 4H-benzo[b]pyran derivatives in the presence of a highly efficient molecular sieve-supported zinc catalyst
Magyar, Agnes
Hell, Zoltan
GREEN PROCESSING AND SYNTHESIS, 2018, 7 (04) : 316 - 322
[8] Highly Efficient One-Pot Three-Component Synthesis and Antimicrobial Activity of 2-Amino-4H-chromene Derivatives
Aminkhani, Ali
Talati, Mina
Sharifi, Roholah
Chalabian, Firouzeh
Katouzian, Fatemeh
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (06) : 1812 - 1819
[9] Synthesis of Pyrimidine Hybrids Based on 4H-Pyran and 4H-Chromene Privileged Structures
Zonouz, Adeleh Moshtaghi
Ghaffari, Parisa
Pourreza, Azita
LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (11) : 993 - 998
[10] Efficient atom economical one-pot multicomponent synthesis of densely functionalized 4H-chromene derivatives
Boominathan, Muthusamy
Nagaraj, Muthupandi
Muthusubramanian, Shanmugam
Krishnakumar, Rajaputi Venkatraman
TETRAHEDRON, 2011, 67 (33) : 6057 - 6064

← 1 2 3 4 5 →