Combined electrochemical/chemical methods for the synthesis and the molecular diversifying of isoindolinone-based heterocyclic scaffolds

Molecular Diversity

Volumn 18, Issue 2, 2014, Pages 323-333

  Palombi, Laura ^a   Di Mola, Antonia ^a   Vignes, Chiara ^a   Massa, Antonio ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

Diversity oriented synthesis; DOS Electrosynthesis; Electron rich alkenes oxidation; Hemiaminals; Imides; Isoindolinones; N acyliminium

Indexed keywords

DI TERT BUTYL 2 (2 ( BETA METHYL) ALLYL 3 OXOISOINDOLIN 1 YL)MALONATE; DI TERT BUTYL 2 (2 ALLYL 3 OXOISOINDOLIN 1 YL)MALONATE; DI TERT BUTYL 2 (2 BENZYL 3 OXOISOINDOLIN 1 YL)MALONATE; DI TERT BUTYL 2 (2 GERANYL 3 OXOISOINDOLIN 1 YL)MALONATE; HETEROCYCLIC COMPOUND; INDOLE; ISOINDOLINONE; UNCLASSIFIED DRUG; INDOLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMICAL ANALYSIS; MOLECULAR LIBRARY; ONE POT SYNTHESIS; PRIORITY JOURNAL; CHEMISTRY; ELECTROCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CHEMISTRY TECHNIQUES, SYNTHETIC; ELECTROCHEMISTRY; HETEROCYCLIC COMPOUNDS; INDOLES; STEREOISOMERISM;

EID: 84898832071     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-013-9502-6     Document Type: Article

References (35)

1. Spandl RJ, Díaz-Gavilán M, O'Connell KMG, Thomas GL, Spring DR (2008) Diversity-oriented synthesis. Chem Rec 8:129-142. doi: 10.1002/tcr.20144
2. Rodriguez R (2012) Target-oriented and diversity-oriented organic synthesis. Mod Tools Synth Complex Bioact Mol 9:513-538. doi: 10.1002/9781118342886.ch15
3. Xu L-M, Liang Y-F, Ye Q-D, Yang Z (2012) Diversity-oriented syntheses of natural products and natural product-like compounds. Org Chem. doi: 10.1002/9783527664801.ch1
4. Eckert H (2012) Diversity oriented syntheses of conventional heterocycles by smart multi component reactions (MCRs) of the last decade. Molecules 17:1074-1102. doi: 10.3390/molecules17011074
5. Zhuang Z-P, Kung M-P, Mu M (1998) Isoindol-1-one analogues of 4-(2 -methoxyphenyl)-1-[2 -[N-(2 -pyridyl)-p-iodobenzamido]ethyl]pipera zine (p-MPPI) as 5-HT1A receptor ligands. J Med Chem 41:157-166. doi: 10.1021/jm970296s
6. Rao IN, Prabhakaran EN, Das SK, Iqbal J (2003) Cobalt-catalyzed one-pot three-component coupling route to β -acetamido carbonyl compounds: a general synthetic protocol for γ -lactams. J Org Chem 68:4079-4082. doi: 10.1021/jo020559c
7. Zhu C, Falck JR (2011) N-Acylsulfonamide assisted tandem C-H olefination/annulation: synthesis of isoindolinones. Org Lett 13:1214-1217. doi: 10.1021/ol200093f
8. Allin SM, Northfield CJ, Page MI, Slawin AMZ (2000) Approaches to the synthesis of non-racemic 3-substituted isoindolinone derivatives. J Chem Soc 1:1715-1721
9. Hesp KD, Bergman RG, Ellman JA (2012) Rhodium-catalyzed synthesis of branched amines by direct addition of benzamides to imines. Org Lett 14:2304-2307. doi: 10.1021/ol300723x
10. Angelin M, Rahm M, Fischer A, Brinck T, Ramstrom O (2010) Diastereoselective one-pot tandem synthesis of 3-substituted isoindolinones: a mechanistic investigation. J Org Chem 75:5882-5887. doi: 10.1021/jo100868z
11. Angelin M, Vongvilai P, Fischer A, Ramstrom O (2008) Tandem driven dynamic combinatorial resolution via Henry-iminolactone rearrangement. Chem Commun 768-770. doi: 10.1039/b716521h
12. More V, Rohlmann R, Mancheno OG, Petronzi C, Palombi L, De Rosa A, Di Mola A, Massa A (2012) The first organocatalytic asymmetric synthesis of 3-substituted isoindolinones. RSC Adv 2:3592-3595. doi: 10.1039/C2ra20231j
13. Tiso S, Palombi L, Vignes C, Di Mola A, Massa A (2013) Organocatalysts and sequential asymmetric cascade reactions in the synthesis of functionalized isoindolinones and benzoindolizidinones. RSC Adv 3:19380-19387. doi: 10.1039/c3ra43074j
14. Medimagh R, Marque S, Prim D, Marrot J, Chatti S (2009) Concise synthesis of tricyclic isoindolinones via one-pot cascade multicomponent sequences. Org Lett 11:1817-1820. doi: 10.1021/ol9003965
15. Zhang H, Leng Y, Liu W, Duan W (2012) One-pot synthesis of isoindolinones via three-component Mannich/lactamization cascade reaction. Synth Commun 42:1115-1127. doi: 10.1080/00397911.2010.535948
16. Sun LX, Zeng T, Jiang D, Dai L-Y, Li C-J (2012) Development of a copper(II)-catalyzed three-component tandem synthesis of isoindolinone derivatives. Can J Chem 90:92-99. doi: 10.1139/V11-108
17. Di Mola A, Palombi L, Massa A (2012) Active methylene compounds in the synthesis of 3-substituted isobenzofuranones, isoindolinones and related compounds. Curr Org Chem 16:2302-2320. doi: 10.2174/138527212803520254
18. Petronzi C, Collarile S, Croce G, Filosa R, De Caprariis P, Peduto A, Palombi L, Intintoli V, Di Mola A, Massa A (2012) Synthesis and reactivity of the 3-substituted isoindolinone framework to assemble highly functionalized related structures. Eur J Org Chem 5357-5365. doi: 10.1002/ejoc.201200678
19. Antico P, Capaccio V, Di Mola A, Massa A, Palombi L (2012) Electrochemically initiated tandem and sequential conjugate addition processes: one-pot synthesis of diverse functionalized isoindolinones. Adv Synth Catal 354:1717-1724. doi: 10.1002/adsc.201200065
20. Caruso T, Feroci M, Inesi A, Orsini M, Scettri A, Palombi L (2006) Electrochemically induced addition reactions in the absence of solvent and supporting electrolyte. Adv Synth Catal 348:1942-1947. doi: 10.1002/adsc. 200606082
21. Palombi L, Feroci M, Orsini M, Inesi A (2004) An innovative strategy for electrochemically-promoted addition reactions. Chem Commun 1846-1847. doi: 10.1039/B406512c
22. Shimoda Y, Kotani S, Sugiura M, Nakajima M (2011) Enantioselective double aldol reaction catalyzed by chiral phosphine oxide. Chem Eur J 17:7992-7995. doi: 10.1002/chem.201100917
23. Palombi L, Feroci M, Orsini M, Rossi L, Inesi A (2002) Electrochemical generation of tetraethylammonium N-acetoacetyloxazolidin-2-one enolates: an easy access to alpha-alkylated acetoacetic derivatives. Tetrahedron Lett 43:2881-2884. doi: 10.1016/S0040-4039(02)00464-1
24. Feroci M, Inesi A, Palombi L, Sotgiu G (2002) Electrogenerated base-induced N-acylation of chiral oxazolidin-2-ones. Part 2. J Org Chem 67:1719-1721. doi: 10.1021/jo016323a
25. Feroci M, Inesi A, Palombi L, Rossi L (2001) Electrochemical generation of chiral oxazolidin-2-ones anions: a new procedure for the highly diastereoselective conjugate addition to nitroalkenes. Tetrahedron 12:2331-2335. doi: 10.1016/S0957-4166(01)00385-8
26. Feroci M, Casadei MA, Orsini M, Palombi L, Inesi A (2003) Cyanomethyl anion/carbon dioxide system: an electrogenerated carboxylating reagent. Synthesis of carbamates under mild and safe conditions. J Org Chem 68:1548-1551. doi: 10.1021/Jo0266036
27. Piancatelli G (2001) Pyridinium dichromate. e-EROS Encycl Reagents. Org Synth. doi: 10.1002/047084289X.rp290
28. Marson CM (2001) Synthesis via N-acyliminium cyclization of N-heterocyclic ring system related to alkaloids. ARKIVOC 2:1-16
29. Speckamp WN, Hiemstra H (1985) Intramolecular reactions of N-acyliminium intermediates. Tetrahedron 41:4367-4416. doi: 10.1016/S0040-4020(01)82334-6
30. Hellmann H (1957) Amidomethylation. Angew Chem 69:463-471
31. Batey RA, MacKay DB, Santhakumar V (1999) Alkenyl and aryl boronates-mild nucleophiles for the stereoselective formation of functionalized N-heterocycles. J Am Chem Soc 121:5075-5076. doi: 10.1021/JA983801Z
32. Potts D, Stevenson PJ, Thompson N (2000) Expedient synthesis of (+)-trans-5-allylhexahydroindolizidin-3-one. Tetrahedron Lett 41:275-278. doi: 10.1016/S0040-4039(99)02034-1
33. Fieser LF, Fieser M (1967) Reagents for organic synthesis. Wiley, Hoboken
34. Ruano JLG, Fajardo C, Fraile A, Martin MR (2005) m-CPBA/KOH: an efficient reagent for nucleophilic epoxidation of gem-deactivated olefins. J Org Chem 70:4300-4306. doi: 10.1021/jo050131o
35. More V, Di Mola A, Perillo M, De Capraris P, Filosa R, Peduto A, Massa A (2011) The aldol addition of readily enolizable 1,3-dicarbonyl compounds to 2-cyanobenzaldehyde in the synthesis of novel 3-substituted isoindolinones. Synthesis 3027-3031. doi: 10.1055/s-0030-1260125