SALICYLIC ACID AS AN EFFICIENT CATALYST FOR THE DIASTEREOSELECTIVE SYNTHESIS OF DISPIROHYDROQUINOLINES VIA A ONE-POT DOMINO EIGHT-COMPONENT REACTION

被引：7

作者：

Salahi, Sajjad ^{[1
]}

Hazeri, Nourallah ^{[1
]}

Maghsoodlou, Malek Taher ^{[1
]}

Lashkari, Mojtaba ^{[2
]}

Torbati, Niloufar Akbarzadeh ^{[1
]}

Garcia-Granda, Santiago ^{[3
]}

Torre-Fernandez, Laura ^{[3
]}

机构：

[1] Univ Sistan & Baluchestan, Fac Sci, Dept Chem, POB 98135-674, Zahedan, Iran

[2] Velayat Univ, Fac Sci, Iranshahr, Iran

[3] Univ Oviedo, Dept Phys & Analyt Chem, CINN, Oviedo, Spain

来源：

JOURNAL OF THE CHILEAN CHEMICAL SOCIETY | 2018年 / 63卷 / 04期

关键词：

Aromatic aldehydes; Aromatic amines; Meidrum's acid; Dispiro compounds; MULTICOMPONENT REACTIONS; ACETYLENIC ESTERS; ALKYL ISOCYANIDES; TETRAHYDROQUINOLINES; CONSTRUCTION; DERIVATIVES; SEQUENCE;

D O I：

10.4067/S0717-97072018000404159

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Salicylic acid was used as an efficient catalyst for the diastereoselective synthesis of dispirohydroquinoline-bis (Meldrim's acid) derivatives via a one-pot domino eight-component reaction of arylamines, aromatic aldehydes and Meldrum's acid in CH3CN at room temperature. The remarkable advantages offered by this method are inexpensive catalyst, good yields, simple and easy work-up procedure. The characterization of products was done by IR, mass, H-1 NMR, C-13 NMR spectroscopy, and elemental analyses. The stereoselectivity of compounds was confirmed with crystallography and NMR spectroscopy.

引用

页码：4159 / 4164

页数：6

共 50 条

[21] The Efficient One-Pot Reaction of up to Eight Components by the Union of Multicomponent Reactions
Elders, Niels
van der Born, Dion
Hendrickx, Loes J. D.
Timmer, Brian J. J.
Krause, Alrik
Janssen, Elwin
de Kanter, Frans J. J.
Ruijter, Eelco
Orru, Romano V. A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (32) : 5856 - 5859
[22] Sulfamic Acid Catalyzed One-Pot Synthesis of Polyhydroquinolines via the Hantzsch Four Component Condensation Reaction
Foroughifar, Naser
Mobinikhaledi, Akbar
Fard, Mohammad Ali Bodaghi
Moghanian, Hassan
Ebrahimi, Sattar
SYNTHESIS AND REACTIVITY IN INORGANIC METAL-ORGANIC AND NANO-METAL CHEMISTRY, 2009, 39 (03) : 161 - 164
[23] One-Pot Synthesis of Novel Spiro[quinazoline/pyrimidine]ones via Multi Component Reaction
Meshram, Gangadhar
Wagh, Pramod
Deshpande, Shruti
Amratlal, Vipul
LETTERS IN ORGANIC CHEMISTRY, 2013, 10 (06) : 445 - 450
[24] TfOH-Catalyzed One-Pot Domino Reaction for Diastereoselective Synthesis of Polysubstituted Tetrahydrospiro[carbazole-1,3′-indoline]s
Yang, Ren-Yin
Sun, Jing
Tao, Yao
Sun, Qin
Yan, Chao-Guo
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (24) : 13277 - 13287
[25] An efficient one-pot method for the synthesis of novel ferrocene-triamide conjugates via pseudo five-component reaction
Teimouri, Mohammad Bagher
Akbari-Moghaddam, Peyman
TETRAHEDRON, 2011, 67 (33) : 5928 - 5934
[26] A facile one-pot domino reaction for the stereoselective synthesis of acryl derivatives promoted by Ca(OTf)2
Yaragorla, Srinivasarao
Saini, Pyare Lal
Pareek, Abhishek
Almansour, Abdulrahman I.
Arumugam, Natarajan
TETRAHEDRON LETTERS, 2016, 57 (19) : 2034 - 2038
[27] An efficient synthesis of new khellactone-type compounds using potassium hydroxide as catalyst via one-pot, three-component reaction
Karami, B.
Eskandari, K.
Khodabakhshi, S.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2014, 11 (03) : 631 - 637
[28] Bismuth triflate: A highly efficient catalyst for the synthesis of bio-active coumarin compounds via one-pot multi-component reaction
El Aleem, Mahmoud. Abd
El-Remaily, Ali. Ali.
CHINESE JOURNAL OF CATALYSIS, 2015, 36 (07) : 1124 - 1130
[29] An efficient domino one-pot synthesis of novel spirofuran-indenoquinoxalines by vinyltriphenylphosphonium salts
Yazdani-Elah-Abadi, Afshin
Maghsoodlou, Malek-Taher
Mohebat, Razieh
Heydari, Reza
JOURNAL OF CHEMICAL SCIENCES, 2017, 129 (06) : 691 - 698
[30] Tartaric acid: a natural, green and highly efficient catalyst for the one-pot synthesis of functionalized piperidines
Aboonajmi, Jasem
Maghsoodlou, Malek Taher
Hazeri, Nourallah
Lashkari, Mojtaba
Kangani, Mehrnoosh
RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (11) : 8057 - 8065

← 1 2 3 4 5 →