Recent Developments in Utility of Green Multi-component Reactions for the Efficient Synthesis of Polysubstituted Pyrans, Thiopyrans, Pyridines, and Pyrazoles

Overview

Journal Mol Divers

Date 2015 Apr 21

PMID 25894364

Citations 3

Authors

Mohamed Hilmy Elnagdi

Moustafa Sherief Moustafa

Saleh Mohammed Al-Mousawi

Ramadan Ahmed Mekheimer

Kamal Usef Sadek

Affiliations

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Abstract

Developments made since 2010 in the utilization of multi-component reactions as green efficient methodologies for the synthesis of polysubstituted pyrans, thiopyrans, pyridines, and pyrazoles are reviewed and the mechanisms of these processes are discussed. Reference is made to classical older synthetic methods developed earlier in our laboratories.

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References

Siddiqui N, Ahsan W, Alam M, Ali R, Srivastava K . Design, synthesis and evaluation of anticonvulsant activity of pyridinyl-pyrrolidones: a pharmacophore hybrid approach. Arch Pharm (Weinheim). 2011; 345(3):185-94. DOI: 10.1002/ardp.201100140. View

Hill M . Recent strategies for the synthesis of pyridine derivatives. Chemistry. 2010; 16(40):12052-62. DOI: 10.1002/chem.201001100. View

Al-Matar H, Khalil K, Adam A, Elnagdi M . Green one pot solvent-free synthesis of pyrano[2,3-c]-pyrazoles and pyrazolo[1,5-a]pyrimidines. Molecules. 2010; 15(9):6619-29. PMC: 6257727. DOI: 10.3390/molecules15096619. View

Chebanov V, Saraev V, Desenko S, Chernenko V, Knyazeva I, Groth U . Tuning of chemo- and regioselectivities in multicomponent condensations of 5-aminopyrazoles, dimedone, and aldehydes. J Org Chem. 2008; 73(13):5110-8. DOI: 10.1021/jo800825c. View

Abdelrazek F, Michael F, Mohamed A . Synthesis and molluscicidal activity of some 1,3,4-triaryl-5-chloropyrazole, pyrano[2,3-c]pyrazole, pyrazolylphthalazine and pyrano[2,3-d]thiazole derivatives. Arch Pharm (Weinheim). 2006; 339(6):305-12. DOI: 10.1002/ardp.200500259. View

Zhang X, Li X, Fan X, Wang X, Li D, Qu G . Ionic liquid promoted preparation of 4H-thiopyran and pyrimidine nucleoside-thiopyran hybrids through one-pot multi-component reaction of thioamide. Mol Divers. 2008; 13(1):57-61. DOI: 10.1007/s11030-008-9098-4. View

Elnagdi N, Al-Hokbany N . Organocatalysis in synthesis: L-proline as an enantioselective catalyst in the synthesis of pyrans and thiopyrans. Molecules. 2012; 17(4):4300-12. PMC: 6268709. DOI: 10.3390/molecules17044300. View

M Al-Zaydi K, Borik R, Mekheimer R, Elnagdi M . Green chemistry: a facile synthesis of polyfunctionally substituted thieno[3,4-c]pyridinones and thieno[3,4-d]pyridazinones under neat reaction conditions. Ultrason Sonochem. 2010; 17(5):909-15. DOI: 10.1016/j.ultsonch.2009.12.008. View

Sadek K, Ahmed Mekheimer R, Mohamed T, Moustafa M, Elnagdi M . Regioselectivity in the multicomponent reaction of 5-aminopyrazoles, cyclic 1,3-diketones and dimethylformamide dimethylacetal under controlled microwave heating. Beilstein J Org Chem. 2012; 8:18-24. PMC: 3302079. DOI: 10.3762/bjoc.8.3. View

10.

Nikpassand M, Mamaghani M, Shirini F, Tabatabaeian K . A convenient ultrasound-promoted regioselective synthesis of fused polycyclic 4-aryl-3-methyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridines. Ultrason Sonochem. 2009; 17(2):301-5. DOI: 10.1016/j.ultsonch.2009.08.001. View

11.

Echevarria A, Martin M, Perez C, Rozas I . Synthesis of 4-alkylpyrazoles as inhibitors of liver alcohol dehydrogenase. Arch Pharm (Weinheim). 1994; 327(5):303-5. DOI: 10.1002/ardp.19943270507. View

12.

Sun J, Xia E, Wu Q, Yan C . Synthesis of 3,4-dihydropyridin-2(1H)-ones and 3,4-dihydro-2H-pyrans via Four-component reactions of aromatic aldehydes, cyclic 1,3-carbonyls, arylamines, and dimethyl acetylenedicarboxylate. ACS Comb Sci. 2011; 13(4):421-6. DOI: 10.1021/co200045t. View

13.

Kumar D, Reddy V, Sharad S, Dube U, Kapur S . A facile one-pot green synthesis and antibacterial activity of 2-amino-4H-pyrans and 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes. Eur J Med Chem. 2009; 44(9):3805-9. DOI: 10.1016/j.ejmech.2009.04.017. View

14.

Chebanov V, Saraev V, Desenko S, Chernenko V, Shishkina S, Shishkin O . One-pot, multicomponent route to pyrazoloquinolizinones. Org Lett. 2007; 9(9):1691-4. DOI: 10.1021/ol070411l. View

15.

Shi F, Li C, Xia M, Miao K, Zhao Y, Tu S . Green chemoselective synthesis of thiazolo[3,2-a]pyridine derivatives and evaluation of their antioxidant and cytotoxic activities. Bioorg Med Chem Lett. 2009; 19(19):5565-8. DOI: 10.1016/j.bmcl.2009.08.046. View

16.

El-borai M, Rizk H, Abd-Aal M, El-Deeb I . Synthesis of pyrazolo[3,4-b]pyridines under microwave irradiation in multi-component reactions and their antitumor and antimicrobial activities - Part 1. Eur J Med Chem. 2011; 48:92-6. DOI: 10.1016/j.ejmech.2011.11.038. View

17.

Safari J, Banitaba S, Dehghan Khalili S . Ultrasound-promoted an efficient method for one-pot synthesis of 2-amino-4,6-diphenylnicotinonitriles in water: a rapid procedure without catalyst. Ultrason Sonochem. 2012; 19(5):1061-9. DOI: 10.1016/j.ultsonch.2012.01.005. View

18.

Moustafa M, Al-Mousawi S, Hilmy N, Ibrahim Y, Liermann J, Meier H . Unexpected behavior of enaminones: interesting new routes to 1,6-naphthyridines, 2-oxopyrrolidines and pyrano[4,3,2-de][1,6]naphthyridines. Molecules. 2012; 18(1):276-86. PMC: 6270018. DOI: 10.3390/molecules18010276. View

19.

Zhang G, Zhang Y, Yan J, Chen R, Wang S, Ma Y . One-pot enantioselective synthesis of functionalized pyranocoumarins and 2-amino-4H-chromenes: discovery of a type of potent antibacterial agent. J Org Chem. 2011; 77(2):878-88. DOI: 10.1021/jo202020m. View

20.

Evdokimov N, Magedov I, Kireev A, Kornienko A . One-step, three-component synthesis of pyridines and 1,4-dihydropyridines with manifold medicinal utility. Org Lett. 2006; 8(5):899-902. DOI: 10.1021/ol052994+. View