L-Proline Catalyzed One-pot Synthesis of Polysubstituted Pyridine System Incorporating Benzothiazole Moiety Sustainable Sonochemical Approach

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 13

PMID 35558590

Authors

Hamada Mohamed Ibrahim

Wael Abdelgayed Ahmed Arafa

Haider Behbehani

Affiliations

Soon will be listed here.

Abstract

The efficient, highly convenient synthesis of polysubstituted pyridine derivatives was established the reaction of -(benzothiazol-2-yl)-2-cyanoacetamides with an assortment of arylidene malononitriles and arylidene ethyl cyanoacetates in the presence of l-proline as an efficient organocatalyst for this type of ultrasonic-mediated Michael addition. The mechanistic pathway and factors affecting this reaction were also established. The main characteristics of this procedure are high yields, use of a cost-effective catalyst, and easy work-up and purification.

Citing Articles

Green Protocol for the Novel Synthesis of Thiochromeno[4,3-]pyridine and Chromeno[4,3-]pyridine Derivatives Utilizing a High-Pressure System.

Behbehani H, Dawood K, Aryan F, Ibrahim H ACS Omega. 2021; 6(49):34065-34074.

PMID: 34926954 PMC: 8675170. DOI: 10.1021/acsomega.1c05347.

TFA-catalyzed Q-Tube Reactor-Assisted Strategy for the Synthesis of Pyrido[1,2-][1,2,4]triazine and Pyrido[1',2':2,3][1,2,4]triazino[5,6-]indole Derivatives.

Ibrahim H, Behbehani H ACS Omega. 2021; 6(24):16086-16099.

PMID: 34179654 PMC: 8223412. DOI: 10.1021/acsomega.1c01980.

High pressure assisted synthetic approach for novel 6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-b]pyridine and 5,6-dihydrobenzo[h]quinoline derivatives and their assessment as anticancer agents.

Behbehani H, Aryan F, Dawood K, Ibrahim H Sci Rep. 2020; 10(1):21691.

PMID: 33303858 PMC: 7728779. DOI: 10.1038/s41598-020-78590-x.

The first Q-Tube based high-pressure synthesis of anti-cancer active thiazolo[4,5-c]pyridazines via the [4 + 2] cyclocondensation of 3-oxo-2-arylhydrazonopropanals with 4-thiazolidinones.

Ibrahim H, Behbehani H Sci Rep. 2020; 10(1):6492.

PMID: 32300148 PMC: 7162912. DOI: 10.1038/s41598-020-63453-2.

Synthetic Strategy for Pyrazolo[1,5-]pyridine and Pyrido[1,2-]indazole Derivatives through AcOH and O-Promoted Cross-dehydrogenative Coupling Reactions between 1,3-Dicarbonyl Compounds and -Amino-2-iminopyridines.

Behbehani H, Ibrahim H ACS Omega. 2019; 4(12):15289-15303.

PMID: 31552376 PMC: 6751734. DOI: 10.1021/acsomega.9b02430.

References

Manning J, Davies H . One-pot synthesis of highly functionalized pyridines via a rhodium carbenoid induced ring expansion of isoxazoles. J Am Chem Soc. 2008; 130(27):8602-3. PMC: 2921945. DOI: 10.1021/ja803139k. View

Donohoe T, Basutto J, Bower J, Rathi A . Heteroaromatic synthesis via olefin cross-metathesis: entry to polysubstituted pyridines. Org Lett. 2011; 13(5):1036-9. DOI: 10.1021/ol103088r. View

Deng J, Paone D, Ginnetti A, Kurihara H, Dreher S, Weissman S . Copper-facilitated Suzuki reactions: application to 2-heterocyclic boronates. Org Lett. 2008; 11(2):345-7. DOI: 10.1021/ol802556f. View

Ueda A, Umeno T, Doi M, Akagawa K, Kudo K, Tanaka M . Helical-Peptide-Catalyzed Enantioselective Michael Addition Reactions and Their Mechanistic Insights. J Org Chem. 2016; 81(15):6343-56. DOI: 10.1021/acs.joc.6b00982. View

Ibrahim H, Behbehani H . Synthesis of a new class of Pyridazin-3-one and 2-amino-5-arylazopyridine derivatives and their utility in the synthesis of fused azines. Molecules. 2014; 19(2):2637-54. PMC: 6272007. DOI: 10.3390/molecules19022637. View

Bharti N, Maurya M, Naqvi F, Azam A . Synthesis and antiamoebic activity of new cyclooctadiene ruthenium(II) complexes with 2-acetylpyridine and benzimidazole derivatives. Bioorg Med Chem Lett. 2000; 10(20):2243-5. DOI: 10.1016/s0960-894x(00)00446-7. View

Banerjee B . Recent developments on ultrasound-assisted one-pot multicomponent synthesis of biologically relevant heterocycles. Ultrason Sonochem. 2016; 35(Pt A):15-35. DOI: 10.1016/j.ultsonch.2016.10.010. View

Wei M, Peng X, Xing L, Dai Y, Huang R, Geng M . Design, synthesis and biological evaluation of a series of novel 2-benzamide-4-(6-oxy-N-methyl-1-naphthamide)-pyridine derivatives as potent fibroblast growth factor receptor (FGFR) inhibitors. Eur J Med Chem. 2018; 154:9-28. DOI: 10.1016/j.ejmech.2018.05.005. View

Santhosh Kumar G, Poornachandra Y, Gunda S, Ratnakar Reddy K, Mohmed J, Shaik K . Synthesis of novel hetero ring fused pyridine derivatives; Their anticancer activity, CoMFA and CoMSIA studies. Bioorg Med Chem Lett. 2018; 28(13):2328-2337. DOI: 10.1016/j.bmcl.2018.04.031. View

10.

Keri R, Patil M, Patil S, Budagumpi S . A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry. Eur J Med Chem. 2014; 89:207-51. DOI: 10.1016/j.ejmech.2014.10.059. View

11.

Bandyopadhyay D, Mukherjee S, Turrubiartes L, Banik B . Ultrasound-assisted aza-Michael reaction in water: a green procedure. Ultrason Sonochem. 2011; 19(4):969-73. DOI: 10.1016/j.ultsonch.2011.11.009. View

12.

Fernandez M, Uria U, Orbe L, Vicario J, Reyes E, Carrillo L . Ethyl glyoxylate N-tosylhydrazone as sulfonyl-transfer reagent in base-catalyzed sulfa-Michael reactions. J Org Chem. 2013; 79(1):441-5. DOI: 10.1021/jo402518q. View

13.

Riaz S, Khan I, Bajda M, Ashraf M, Qurat-Ul-Ain , Shaukat A . Pyridine sulfonamide as a small key organic molecule for the potential treatment of type-II diabetes mellitus and Alzheimer's disease: In vitro studies against yeast α-glucosidase, acetylcholinesterase and butyrylcholinesterase. Bioorg Chem. 2015; 63:64-71. DOI: 10.1016/j.bioorg.2015.09.008. View

14.

Bondock S, Fadaly W, Metwally M . Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. Eur J Med Chem. 2010; 45(9):3692-701. DOI: 10.1016/j.ejmech.2010.05.018. View

15.

Liu J, Wang Z, Levin A, Emge T, Rablen P, Floyd D . N-methylimidazole promotes the reaction of homophthalic anhydride with imines. J Org Chem. 2014; 79(16):7593-9. PMC: 4136697. DOI: 10.1021/jo501316m. View

16.

Wu L, Jin R, Li L, Hu X, Cheng T, Liu G . A Michael Addition-Asymmetric Transfer Hydrogenation One-Pot Enantioselective Tandem Process for Syntheses of Chiral γ-Secondary Amino Alcohols. Org Lett. 2017; 19(12):3047-3050. DOI: 10.1021/acs.orglett.7b00823. View

17.

Luzung M, Patel J, Yin J . A mild Negishi cross-coupling of 2-heterocyclic organozinc reagents and aryl chlorides. J Org Chem. 2010; 75(23):8330-2. DOI: 10.1021/jo1018798. View

18.

Palomo C, Oiarbide M, Mielgo A . Unveiling reliable catalysts for the asymmetric nitroaldol (Henry) reaction. Angew Chem Int Ed Engl. 2004; 43(41):5442-4. DOI: 10.1002/anie.200460506. View

19.

Pizzuti L, Piovesan L, Flores A, Quina F, Pereira C . Environmentally friendly sonocatalysis promoted preparation of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-1H-pyrazoles. Ultrason Sonochem. 2009; 16(6):728-31. DOI: 10.1016/j.ultsonch.2009.02.005. View

20.

Behbehani H, Ibrahim H, Makhseed S, Elnagdi M, Mahmoud H . 2-Aminothiophenes as building blocks in heterocyclic synthesis: synthesis and antimicrobial evaluation of a new class of pyrido[1,2-a]thieno[3,2-e]pyrimidine, quinoline and pyridin-2-one derivatives. Eur J Med Chem. 2012; 52:51-65. DOI: 10.1016/j.ejmech.2012.03.004. View