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Microwave-Assisted and Thermal Synthesis of Calix[4]arene Derivatives

By:Al-Douh, MH (Al-Douh, M. H.)[ 1 ] ; Ali, Y (Ali, Y.)[ 2 ] ; Abd Hamid, S (Abd Hamid, S.)[ 3 ] RUSSIAN JOURNAL OF ORGANIC CHEMISTRY

Volume: 56 Issue: 7 Pages: 1251-1257 DOI: 10.1134/S1070428020070209 Published: JUL 2020

Document Type: Article View Journal Impact

Abstract

Sometert-butylcalix[4]arene derivatives were synthesized by thermal and microwave methods. The microwave method was conducted in two ways: (1) all the reactants were added in one batch and (2) the reactants were added in two batches under different conditions. Tetrabutylammonium iodide (TBAI) was used in both methods, and its effect on the reaction rate was studied. In general, the duration of the microwave-assisted reactions in the presence of TBAI, especially in the two-batch method, was shorter, and the yields were higher, than in the thermal reaction. The highest yield of (S)-glycidyl calixarene derivative by the thermal method was obtained by using K(2)CO(3)as a base with MeCN as a solvent in the presence of TBAI, while the lowest yield of the same compound was observed when using acetone in the absence of TBAI. All the synthesized calix[4]arene derivatives were characterized by(1)H and(13)C NMR experiments.

Keywords

Author Keywords:microwave synthesis; calix[4]arenes; tetrabutylammonium iodide

Author Information

Reprint Address:

Sarhad Univ Sci & Informat Technol, Dept Chem, Peshawar 25000, Pakistan.

International Islamic University Malaysia Int Islamic Univ Malaysia, Kulliyyah Sci, Kuantan 25200, Pahang, Malaysia.

Corresponding Address: Ali, Y (corresponding author)

       Sarhad Univ Sci & Informat Technol, Dept Chem, Peshawar 25000, Pakistan.

Corresponding Address: Abd Hamid, S (corresponding author)

Int Islamic Univ Malaysia, Kulliyyah Sci, Kuantan 25200, Pahang, Malaysia.

Addresses:

       [ 1 ] Hadhramout Univ, Fac Sci, Chem Dept, Mukalla 50511, Hadhramout, Yemen        [ 2 ] Sarhad Univ Sci & Informat Technol, Dept Chem, Peshawar 25000, Pakistan

[ 3 ] Int Islamic Univ Malaysia, Kulliyyah Sci, Kuantan 25200, Pahang, Malaysia E-mail Addresses:[email protected]; [email protected]

Funding

Funding Agency Grant Number

Malaysian government   

International Islamic University Malaysia (IIUM) Fund  ERGS12-017-0017 View funding text   

Publisher

MAIK NAUKA/INTERPERIODICA/SPRINGER, 233 SPRING ST, NEW YORK, NY 10013-1578 USA

Journal Information

Impact Factor: Journal Citation Reports

Categories / Classification

Research Areas: Chemistry

Web of Science Categories: Chemistry, Organic See more data fields

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4/1/2021 Web of Science [v.5.35] - Web of Science Core Collection Full Record

https://apps-webofknowledge-com.ezproxy.um.edu.my/full_record.do?product=WOS&search_mode=GeneralSearch&qid=2&SID=E6sOB4U7hjQ… 2/2 (from Web of Science Core Collection)

Cited References: 10

Showing 10 of 10 View All in Cited References page

Design and synthesis of calixarene By: Agrawal, Y. K.; Pancholi, J. P.; Vyas, J. M.

JOURNAL OF SCIENTIFIC & INDUSTRIAL RESEARCH   Volume: 68   Issue: 9   Pages: 745-768   Published: SEP 2009

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A Critical Overview on the Effect of Microwave Irradiation in Organic Synthesis By: Diaz-Ortiz, A.; Prieto, P.; de la Hoz, A.

CHEMICAL RECORD   Volume: 19   Issue: 1   Special Issue: SI   Pages: 85-97   Published: JAN 2019

Times Cited: 39

Changing Perspectives on the Strategic Use of Microwave Heating in Organic Synthesis By: Dudley, Gregory B.; Stiegman, A. E.

CHEMICAL RECORD   Volume: 18   Issue: 3   Pages: 381-389   Published: MAR 2018

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Title: [not available]

By: Gutsche, C.D.

Calixarenes: An Introduction     Published: 2008 Publisher: Roy. Soc. Chem., Cambridge

Times Cited: 6

CONFORMATIONS AND STRUCTURES OF TETRA-O-ALKYL-PARA-TERT-BUTYLCALIX[4]ARENES - HOW IS THE CONFORMATION OF CALIX[4]ARENES IMMOBILIZED

By: IWAMOTO, K; ARAKI, K; SHINKAI, S

JOURNAL OF ORGANIC CHEMISTRY   Volume: 56   Issue: 16   Pages: 4955-4962   Published: AUG 2 1991

Times Cited: 382

Controlled microwave heating in modern organic synthesis By: Kappe, CO

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   Volume: 43   Issue: 46   Pages: 6250-6284   Published: 2004

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Title: [not available]

By: Neri, P.; Sessler, J. L.; Wang, M.-X.

Calixarenes and Beyond     Published: 2016 Publisher: Springer

Times Cited: 11

Synthesis of new calix[4]arene based chiral ligands bearing beta-amino alcohol groups and their application in asymmetric transfer hydrogenation

By: Quintard, Adrien; Darbost, Ulrich; Vocanson, Francis; et al.

TETRAHEDRON-ASYMMETRY   Volume: 18   Issue: 16   Pages: 1926-1933   Published: AUG 22 2007

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Calixarenes: A Versatile Class of Macrocyclic Compounds Edited by: Vicens, J.; Bohmer, V.

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Applications of calixarenes in cancer chemotherapy: facts and perspectives By: Yousaf, Ali; Abd Hamid, Shafida; Bunnori, Noraslinda M.; et al.

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