Highly Efficient and Diastereoselective Synthesis of New Pyrazolylpyrrolizine and Pyrazolylpyrrolidine Derivates by a Three-component Domino Process

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2014 Apr 10

PMID 24714191

Citations 2

Authors

Jairo Quiroga

Jaime Galvez

Rodrigo Abonia

Braulio Insuasty

Alejandro Ortiz

Justo Cobo

Manuel Nogueras

Affiliations

Soon will be listed here.

Abstract

Diastereoselective reactions between 4-formylpyrazoles, N-substituted maleimides and glycine derivates led to new series of pyrazolyldipyrrolo [3,4-a:3',4'-f]pyrrolizines and pyrazolylpyrrolo[3,4-c]pyrroles in good yields. The reactions proceeded by a domino process through azomethine ylides formed in situ via a 1,3-dipolar cycloaddition reaction.

Citing Articles

Synthesis and spectroscopic and structural characterization of spiro[indoline-3,3'-indolizine]s formed by 1,3-dipolar cycloadditions between isatins, pipecolic acid and an electron-deficient alkene.

Romo P, Quiroga J, Cobo J, Glidewell C Acta Crystallogr C Struct Chem. 2021; 77(Pt 9):496-504.

PMID: 34482292 PMC: 8418672. DOI: 10.1107/S2053229621007142.

Recent Developments on Five-Component Reactions.

Ma X, Zhi S, Zhang W Molecules. 2021; 26(7).

PMID: 33915870 PMC: 8037922. DOI: 10.3390/molecules26071986.

References

Bashiardes G, Safir I, Said Mohamed A, Barbot F, Laduranty J . Microwave-assisted [3 + 2] cycloadditions of azomethine ylides. Org Lett. 2003; 5(25):4915-8. DOI: 10.1021/ol0361195. View

Stevens K, Tyrrell A, Skerratt S, Robertson J . Synthesis of NP25302. Org Lett. 2011; 13(22):5964-7. DOI: 10.1021/ol202381m. View

Rotstein D, Melville C, Padilla F, Cournoyer D, Lee E, Lemoine R . Novel hexahydropyrrolo[3,4-c]pyrrole CCR5 antagonists. Bioorg Med Chem Lett. 2010; 20(10):3116-9. DOI: 10.1016/j.bmcl.2010.03.095. View

Petrovskaia O, Taylor B, Hauze D, Carroll P, Joullie M . Investigations of the reaction mechanisms of 1,2-indanediones with amino acids. J Org Chem. 2001; 66(23):7666-75. DOI: 10.1021/jo0105179. View

Garner P, Umit Kaniskan H . Synthesis of highly functionalized pyrrolidines via a mild one-pot, three-component 1,3-dipolar cycloaddition process. J Org Chem. 2005; 70(26):10868-71. DOI: 10.1021/jo051926y. View

Georgiou D, Toutountzoglou V, Muir K, Hadjipavlou-Litina D, Elemes Y . Synthesis of sulfur containing dihydro-pyrrolo derivatives and their biological evaluation as antioxidants. Bioorg Med Chem. 2012; 20(17):5103-9. DOI: 10.1016/j.bmc.2012.07.014. View

Wang G, Chen Y, Wang S, Gentles R, Sowin T, Kati W . Design, synthesis, and structural analysis of influenza neuraminidase inhibitors containing pyrrolidine cores. J Med Chem. 2001; 44(8):1192-201. DOI: 10.1021/jm000468c. View

Sharma P, Kumar S, Kumar P, Kaushik P, Kaushik D, Dhingra Y . Synthesis and biological evaluation of some pyrazolylpyrazolines as anti-inflammatory-antimicrobial agents. Eur J Med Chem. 2010; 45(6):2650-5. DOI: 10.1016/j.ejmech.2010.01.059. View

Kalgutkar A, Crews B, Marnett L . Design, synthesis, and biochemical evaluation of N-substituted maleimides as inhibitors of prostaglandin endoperoxide synthases. J Med Chem. 1996; 39(8):1692-703. DOI: 10.1021/jm950872p. View

10.

Quiroga J, Galvez J, Cobo J, Glidewell C . Two methyl 3-(1H-pyrazol-4-yl)octahydropyrrolo[3,4-c]pyrrole-1-carboxylates form different hydrogen-bonded sheets. Acta Crystallogr C. 2013; 69(Pt 8):915-9. DOI: 10.1107/S0108270113017563. View

11.

Fustero S, Sanchez-Rosello M, Barrio P, Simon-Fuentes A . From 2000 to mid-2010: a fruitful decade for the synthesis of pyrazoles. Chem Rev. 2011; 111(11):6984-7034. DOI: 10.1021/cr2000459. View

12.

Barker G, McGrath J, Klapars A, Stead D, Zhou G, Campos K . Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: in situ react IR spectroscopic monitoring, scope, and synthetic applications. J Org Chem. 2011; 76(15):5936-53. DOI: 10.1021/jo2011347. View

13.

Toyooka N, Zhou D, Nemoto H, Tezuka Y, Kadota S, Andriamaharavo N . Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B. J Org Chem. 2009; 74(17):6784-91. PMC: 2747258. DOI: 10.1021/jo901100m. View

14.

Cui P, Xu L, Shi Z, Gan L . Synthesis of decahydropyrrolo[2,1,5-cd]indolizine through consecutive [2 + 3] cycloadditions and 6-exo-trig cyclization. J Org Chem. 2011; 76(10):4210-2. DOI: 10.1021/jo200601y. View

15.

Ramon D, Yus M . Asymmetric multicomponent reactions (AMCRs): the new frontier. Angew Chem Int Ed Engl. 2005; 44(11):1602-34. DOI: 10.1002/anie.200460548. View

16.

Kudryavtsev K, Irkha V . Three-component synthesis of polysubstituted homoproline analogs. Molecules. 2007; 10(7):755-61. PMC: 6147630. DOI: 10.3390/10070755. View

17.

Yao S, Gallenkamp D, Wolfel K, Luke B, Schindler M, Scherkenbeck J . Synthesis and SERCA activities of structurally simplified cyclopiazonic acid analogues. Bioorg Med Chem. 2011; 19(15):4669-78. DOI: 10.1016/j.bmc.2011.06.001. View

18.

Deslandes S, Lamoral-Theys D, Frongia C, Chassaing S, Bruyere C, Lozach O . Synthesis and biological evaluation of analogs of the marine alkaloids granulatimide and isogranulatimide. Eur J Med Chem. 2012; 54:626-36. DOI: 10.1016/j.ejmech.2012.06.012. View

19.

Quiroga J, Galvez J, Cobo J, Glidewell C . Methyl (3aRS,3cRS,6cSR,7RS,8RS,8aSR)-2,5-bis(4-chlorophenyl)-7,9-bis(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4,6-tetraoxododecahydro-1H-dipyrrolo[3,4-a:3',4'-f]pyrrolizine-3b-carboxylate dimethylformamide disolvate: a three-dimensional hydrogen-bonded.... Acta Crystallogr C. 2012; 68(Pt 11):o439-42. DOI: 10.1107/S0108270112039856. View

20.

Ruijter E, Scheffelaar R, Orru R . Multicomponent reaction design in the quest for molecular complexity and diversity. Angew Chem Int Ed Engl. 2011; 50(28):6234-46. DOI: 10.1002/anie.201006515. View