N1,N1,N2,N2-Tetramethyl-N1,N2-bis(sulfo)ethane-1,2-diaminium chloride as a highly efficient catalyst for synthesis of some nitrogen- and oxygen-containing heterocyclic compounds

Dashtizadeh, Maryam; Khalili, Maryam; Reghbat, Fatemeh; Abdi, Eshagh; Bahadori, Zahra; Sadripour, Zahra; Zare, Abdolkarim; Didehban, Khadijeh; Sajadikhah, Seyed Sajad

doi:10.30473/icc.2018.40557.1441

Document Type : Original Research Article

Authors

¹ Department of Chemistry, Payame Noor University, P.O. Box 19395-4697 Tehran, Iran

² Department of Chemistry, Payame Noor University of Bushehr, Bushehr, Iran

³ Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran

https://doi.org/10.30473/icc.2018.40557.1441

Abstract

In this research, a Brønsted acidic ionic liquid namely N1,N1,N2,N2-tetramethyl-N1,N2-bis(sulfo)ethane-1,2-diaminium chloride {[TMBSED][Cl]2} was employed as a highly efficient catalyst for the solvent-free production of some nitrogen- and oxygen-containing heterocyclic compounds including: (i) polyhydroquinolines (from arylaldehydes, dimedone, β-ketoesters and ammonium acetate), (ii) 3,4-dihydropyrimidin-2-(1H)-ones/thiones (from arylaldehydes, β-ketoesters and urea/thiourea), and (iii) 14-aryl-14H-dibenzo[a,j]xanthenes (from aromatic aldehydes and β-naphthol). In all cases, the heterocycles were obtained in high yields and in short reaction times. The salient features of using [TMBSED][Cl]2 in the reactions, include effectiveness, generality, simple preparation of the catalyst from inexpensive and easy available reactants, achieving the reactions under solvent-free conditions, synthesis of the products with high yields in short reaction times and need to milder conditions compared with many reported methods for the preparation of the aforesaid organic compounds.

Graphical Abstract

Keywords

Main Subjects

Organic chemistry

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Iranian chemical communication

N1,N1,N2,N2-Tetramethyl-N1,N2-bis(sulfo)ethane-1,2-diaminium chloride as a highly efficient catalyst for synthesis of some nitrogen- and oxygen-containing heterocyclic compounds

References

References

Volume 7, Issue 3, pp. 160-229, Serial No. 24
July 2019
Pages 160-173

N1,N1,N2,N2-Tetramethyl-N1,N2-bis(sulfo)ethane-1,2-diaminium chloride as a highly efficient catalyst for synthesis of some nitrogen- and oxygen-containing heterocyclic compounds

References

References

Volume 7, Issue 3, pp. 160-229, Serial No. 24July 2019Pages 160-173

Volume 7, Issue 3, pp. 160-229, Serial No. 24
July 2019
Pages 160-173