A novel four-component reaction for the synthesis of disubstituted 1,3,4-oxadiazole derivatives

Molecular Diversity

Volumn 15, Issue 2, 2011, Pages 521-527

  Ramazani, Ali ^a   Shajari, Nahid ^a   Mahyari, Amir ^a   Ahmadi, Yavar ^a  

^a UNIVERSITY OF ZANJAN   (Iran)

Author keywords

(N isocyanimino)triphenylphosphorane; 1,3,4 oxadiazole; 4CC; Aromatic carboxylic acid; Aza Wittig reaction; Benzyl amine; Cyclobutanone; MCR

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; AMINE; BENZYL DERIVATIVE; CYCLOBUTANONE DERIVATIVE; BENZYLAMINE DERIVATIVE; CARBOXYLIC ACID; CYCLOBUTANE DERIVATIVE; CYCLOBUTENONE; OXADIAZOLE DERIVATIVE;

ARTICLE; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS; WITTIG REACTION; CHEMISTRY;

BENZYLAMINES; CARBOXYLIC ACIDS; CYCLOBUTANES; OXADIAZOLES;

EID: 79957635000     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-010-9275-0     Document Type: Article

References (23)

1. Yavari I, Hossaini Z, Sabbaghan M (2006) Synthesis of functionalized 5-imino-2, 5-dihydro-furans through the reaction of isocyanides with activated acetylenes in the presence of ethyl bromopyruvate. Mol Divers 10:479-482. doi:10.1007/s11030-006-9034-4 (Pubitemid 46150640)
2. Yavari I, Sabbaghan M, Hossaini Z (2007) Reaction between alkyl isocyanides and isopropylidene meldrum's acid in the presence of bidentate nucleophiles. Mol Divers 11:1-5. doi:10.1007/s11030-006-9052-2 (Pubitemid 46639417)
3. Nasiri F, Nazem F, Pourdavaie K (2007) Chemo-and stereoselective reaction between alkyl isocyanides and dimethyl 1, 3-acetonedicarbocxylate in the presence of acetylenic esters. Mol Divers 11:101-105. doi:10.1007/s11030-007- 9064-6 (Pubitemid 350104535)
4. Shaabani A, Teimouri MB, Bazgir A, Bijanzadeh HR (2003) Introducing a novel class of four-component reactions. Mol Divers 6:199-206. doi:10.1023/B:MODI.0000006759.20910.f1 (Pubitemid 38089856)
5. Ugi I, Werner B, Dömling A (2003) The chemistry of isocyanides, their multicomponent reactions and their libraries. Molecules 8:53-66. doi:10.3390/80100053 (Pubitemid 38990351)
6. Palacios F, Aparicio D, Rubiales G, Alonso C, los Santos JMde (2009) Synthetic applications of intramolecular aza-Wittig reaction for the preparation of heterocyclic compounds. Curr Org Chem 13:810-828. doi:10.2174/ 138527209788167196
7. Stolzenberg H, Weinberger B, Fehlhammer WP, Pühlhofer FG, Weiss R (2005) Free and metal-coordinated (N-isocyanimino) triphenylphosphorane: X-ray structures and selected reactions. Eur J Inorg Chem 21:4263-4271. doi:10.1002/ejic.200500196 (Pubitemid 41587544)
8. Ramazani A, Bodaghi A (2000) One-pot, four-component synthesis of dialkyl [indane-1, 3-dione-2-ylidene]alkoxysuccinates. Tetrahedron Lett 41:567-568. doi:10.1016/S0040-4039 (99) 02066-3 (Pubitemid 30059272)
9. Pakravan P, Ramazani A, Noshiranzadeh N, Sedrpoushan A (2007) One-pot synthesis of fluorine-containing alkenes from in situ-generated stabilized phosphorus ylides. Phosphorus Sulfur 182:545-549. doi:10.1080/10426500601013257
10. Ramazani A, Rahimifard M, Souldozi A (2007) Silica-gel catalyzed stereoselective conversion of stabilized phosphorus ylides to dialkyl (Z)-2-(2-methoxycarbonyl-phenoxy)-2-butenedioates in solvent-free conditions. Phosphorus Sulfur 182:1-5. doi:10.1080/10426500600961571 (Pubitemid 44878934)
11. Ramazani A, Rahimifard M, Noshiranzadeh N, Souldozi A (2007) Dipotassium hydrogen phosphate-catalyzed synthesis of dialkyl 2-(4-fluoro-phenoxy)-2- butendioates from stabilized phosphorus ylides in solvent-free conditions. Phosphorus Sulfur 182:413-417. doi:10.1080/10426500600920007
12. Ramazani A, Ahmadi E, Kazemizadeh AR, Dolatyari L, Noshiranzadeh N, Eskandari I, Souldozi A (2005) One-pot, three-component synthesis of dialkyl 1, 2-dihydroquinoline-2, 3-dicarboxylates from triphenylphosphine, acetylenic esters, and amide derivatives of 2-aminobenzaldehyde in aqueous acetone. Phosphorus Sulphur 180:2419-2422. doi:10.1080/104265090921137 (Pubitemid 43175200)
13. Ramazani A, Shajari N, Gouranlou F (2001) A facile synthetic approach to dimethyl 2-arylamino-3-(triphenylphosphoranylidene) succinates from electron-poor primary arylamines. Phosphorus Sulfur 174:223-227. doi:10.1080/10426500108040246 (Pubitemid 33590257)
14. Ramazani A, Amini I, Massoudi A (2006) Dipotassium hydrogen phosphate powder-catalyzed stereoselective synthesis of N-vinyl pyrazoles in solvent-free conditions. Phosphorus Sulphur 181:2225-2229. doi:10.1080/10426500600614683 (Pubitemid 44385631)
15. Souldozi A, Ramazani A, Bouslimani N, Welter R (2007) The reaction of (N-isocyanimino) triphenylphosphorane with dialkyl acetylenedicarboxylates in the presence of 1, 3-diphenyl-1, 3-propanedione: a novel three-component reaction for the stereoselective synthesis of dialkyl (Z)-2-(5, 7-diphenyl-1, 3, 4-oxadiazepin-2-yl) - 2-butenedioates. Tetrahedron Lett 48:2617-2620. doi:10.1016/j. tetlet.2007.02.010 (Pubitemid 46356461)
16. Souldozi A, Ramazani A (2007) The reaction of (N-isocyanimino) triphenylphosphorane with benzoic acid derivatives: a novel synthesis of 2-aryl-1, 3, 4-oxadiazole derivatives. Tetrahedron Lett 48:1549-1551. doi:10.1016/j.tetlet.2007.01.021 (Pubitemid 46177162)
17. Souldozi A, Ramazani A (2009) (N-Isocyanimino) triphenylphosphorane as an efficient reagent for the synthesis of 1, 3, 4-oxadiazoles from 3-substituted benzoic acid derivatives. Phosphorus Sulfur 184:3191-3198. doi:10.1080/ 10426500802705537
18. Souldozi A, Ramazani A (2009) The reaction of (N-isocyanimino) triphenylphosphorane with anthranilic acid derivatives: onepot synthesis of 2-substituted 1, 3, 4-oxadiazoles via intramolecular aza-Wittig reaction. Phosphorus Sulfur 184:2344-2350. doi:10. 1080/10426500802466684
19. Souldozi A, Ramazani A (2008) Iminophosphoranes mediated one-pot synthesis of 1, 3, 4-oxadiazole derivatives. Arkivoc xvi: 235-242
20. Souldozi A, Ślepokura K, Lis T, Ramazani A (2007) Synthesis and single crystal X-ray structure of 2-(1, 3, 4-oxadiazol-2-yl) aniline. Z Naturforsch B 62 b: 835-840
21. Holla BS, Gonsalves R, Shenoy S (2000) Synthesis and antibacterial studies of a new series of 1, 2-bis (1, 3, 4-oxadiazol-2-yl) ethanes and 1, 2-bis (4-amino-1, 2, 4-triazol-3-yl) ethanes. Eur J Med Chem 35:267-271. doi:10.1016/S0223-5234 (00) 00154-9 (Pubitemid 30165690)
22. Baxendale IR, Ley SV, Martinelli M (2005) The rapid preparation of 2-aminosulfonamide-1, 3, 4-oxadiazoles using polymersupported reagents and microwave heating. Tetrahedron 61:5323-5349. doi:10.1016/j.tet.2005.03.062 (Pubitemid 40693260)
23. Wang Y, Sauer DR, Djuric SW (2006) A simple and efficient one step synthesis of 1, 3, 4-oxadiazoles utilizing polymer-supported reagents and microwave heating. Tetrahedron Lett 47:105-108. doi:10.1016/j.tetlet.2005.10.13 (Pubitemid 41743785)