Guanidinium-based sulfonic acid: an efficient Brønsted acid organocatalyst for the synthesis of fused polycyclic dihydropyridines in water

Guanidinium-based sulfonic acid: an efficient Brønsted acid organocatalyst for the synthesis of... Keywords 1,1,3,3-Tetramethylguanidine  Clorosulfonic acid  Organocatalyst 4-Hydroxycoumarin  Polycyclic dihydropyridine & Ahmad Shaabani a-shaabani@sbu.ac.ir Faculty of Chemistry, Shahid Beheshti University, G. C., P. O. Box 19396-4716, Tehran, Iran 123 7248 A. Shaabani et al. Introduction Polycyclic 1,4-dihydropyridines due to their intriguing molecular structure and remarkable pharmacological efficiency [1–4] are important in discovering new bioactive compounds. This class of building blocks could treat Alzheimer’s disease (Tacripyrimedone) [5–7], open potassium channels (A-278637 and ZM244085) [8– 10], as well as show anti-tumor (I) [11], anti-diarrhea (II) [12, 13], and antimicrobial properties (III) [14] (Fig. 1). Nowadays, the combination of several functional groups in one molecule seems to be a useful tool to optimize properties of biological compounds. Coumarin, as a ‘‘privileged scaffold’’, is a well-known class of heterocyclic compounds, which is present in a variety of natural products as well as a large family of pharmaceutically important agents [15, 16]. Accordingly, their fusion to form a polycyclic fused pyridine ring may potentially provide a class of novel drug candidates with unusual biological activities. Many methods for the synthesis of fused pyridines [17–20] and dihyropyridines [21–23] have been reported. However, most of these methodologies suffer various harsh reaction conditions such as use http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Guanidinium-based sulfonic acid: an efficient Brønsted acid organocatalyst for the synthesis of fused polycyclic dihydropyridines in water

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Publisher
Springer Netherlands
Copyright
Copyright © 2016 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-016-2533-8
Publisher site
See Article on Publisher Site

Abstract

Keywords 1,1,3,3-Tetramethylguanidine  Clorosulfonic acid  Organocatalyst 4-Hydroxycoumarin  Polycyclic dihydropyridine & Ahmad Shaabani a-shaabani@sbu.ac.ir Faculty of Chemistry, Shahid Beheshti University, G. C., P. O. Box 19396-4716, Tehran, Iran 123 7248 A. Shaabani et al. Introduction Polycyclic 1,4-dihydropyridines due to their intriguing molecular structure and remarkable pharmacological efficiency [1–4] are important in discovering new bioactive compounds. This class of building blocks could treat Alzheimer’s disease (Tacripyrimedone) [5–7], open potassium channels (A-278637 and ZM244085) [8– 10], as well as show anti-tumor (I) [11], anti-diarrhea (II) [12, 13], and antimicrobial properties (III) [14] (Fig. 1). Nowadays, the combination of several functional groups in one molecule seems to be a useful tool to optimize properties of biological compounds. Coumarin, as a ‘‘privileged scaffold’’, is a well-known class of heterocyclic compounds, which is present in a variety of natural products as well as a large family of pharmaceutically important agents [15, 16]. Accordingly, their fusion to form a polycyclic fused pyridine ring may potentially provide a class of novel drug candidates with unusual biological activities. Many methods for the synthesis of fused pyridines [17–20] and dihyropyridines [21–23] have been reported. However, most of these methodologies suffer various harsh reaction conditions such as use

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Apr 6, 2016

References

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