Novel and efficient one-pot five-and six-component reactions for the stereoselective synthesis of highly functionalized enaminones and dithiocarbamates

Molecular Diversity

Volumn 15, Issue 2, 2011, Pages 583-594

  Bararjanian, Morteza ^a   Balalaie, Saeed ^a   Rominger, Frank ^b   Movassagh, Barahman ^a   Bijanzadeh, Hamid Reza ^c  

^a K N TOOSI UNIVERSITY OF TECHNOLOGY   (Iran)

^b UNIVERSITY OF HEIDELBERG   (Germany)

^c TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Activeacetylenic compounds; Functionalized e enaminones and Z dithiocarbamates; MCR; One pot five and six component reaction; Sequential Ugi Nucleophilic addition reaction

Indexed keywords

AMINE; DITHIOCARBAMIC ACID DERIVATIVE; ENAMINONE DERIVATIVE; UNCLASSIFIED DRUG; THIOCARBAMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; CHEMICAL MODEL; CHEMISTRY; COMBINATORIAL CHEMISTRY; METHODOLOGY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

AMINES; COMBINATORIAL CHEMISTRY TECHNIQUES; MODELS, CHEMICAL; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THIOCARBAMATES;

EID: 80051567091     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-010-9286-x     Document Type: Article

References (44)

1. Dömling A (2005) The discovery of new isocyanide-based multicomponent reactions. In: Zhu J, Bienaymé H (eds) Multicomponent reaction. Wiely-VCH, Weinheim, pp 76-95
2. Tietze LF (1996) Domino reactions in organic synthesis. Chem Rev 96:115-136. doi:10.1021/cr950027e (Pubitemid 126637714)
3. Tietze LF, Brasche G, Gericke KM (2006) Domino reaction in organic synthesis. Wiely-VCH, Weinheim, pp 542-565
4. Tietze LF, Hauner F (2000) Domino reaction in organic synthesis and approach to efficiency, elegance, ecological, benefit, economic, advantage, and preservation of our resources in chemical transformation. In: Shibasaki M, Stoddart JF (eds) Stimulating concepts in chemistry. Wiely-VCH, Weinheim, pp 39-64
5. Padwa A, Bur SK (2007) The domino way to heterocycles. Tetrahedron 63:5341-5378. doi:10.1016/j.tet.2007.03.158 (Pubitemid 46881030)
6. Dömling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39:3168. doi:10.1002/1521-3773 (20000915) 39:18<3168:AID- ANIE3168>3.0. CO;2-U
7. Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106:17-80. doi:10.1021/cr0505728 (Pubitemid 43159621)
8. Sunderhaus JD, Martin SF (2009) Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds. Chem Eur J 15:1300-1308. doi:10.1002/chem.200802140
9. Keating TA, Armstrong RW (1998) The Ugi five-component condensation using CO2, CS2, and COS as oxidized carbon sources. J Org Chem 63:867-871. doi:10.1021/jo971463z
10. Dömling A, Ugi I (1993) The seven-component reaction. Angew Chem Int Ed Engl 32:563-564. doi:10.1002/anie.199305631
11. Elders N, van der Born D, Hendrickx LJD, Timmer BJJ, Krause A, Janssen E, de Kanter FJJ, Ruijter E, Orru RVA (2009) The efficient one-pot reaction of up to eight components by the union of multicomponent reactions. Angew Chem Int Ed 48:5856-5859. doi:10. 1002/anie.200902683
12. William E, Neuville L, Zhu J (2009) Ugi-post functionalization, from a single set of Ugi-adducts to two distinct heterocycles by microwave-assisted palladium-catalyzed cyclizations: tuning the reaction pathways by ligand switch. J Org Chem 74:3109-3115. doi:10.1021/jo900210x
13. Corres N, Delgado JJ, Garcia-Valverde M, Marcaccini S, Rodriguez T, Rojo J, Torroba T (2008) Synthesis of pseudopeptidic [(5H)-6-oxodibenzo[b, f][1, 5]diazocine-5-yl]arylglycinamides by an Ugi 4CC/Staudinger/aza-Wittig sequence. Tetrahedron 64:2225-2232. doi:10.1016/j.tet.2007.12.028
14. Beck B, Larbig GB, Mejat B, Magnin-Lachaux M, Picard A, Herdtweck E, Dömling A (2003) Short and diverse route toward complex natural product-like macrocycles. Org Lett 5:1047-1050. doi:10.1021/ol034077e (Pubitemid 37141032)
15. Banfi L, Basso A, Guanti G, Kielland N, Repetto C, Riva R (2007) Ugi multicomponent reaction followed by an intramolecular nucleophilic substitution: convergent multicomponent synthesis of 1-sulfonyl 1, 4-diazepan-5-ones and of their benzo-fused derivatives. J Org Chem 72:2151-2160. doi:10.1021/jo062626z (Pubitemid 46418421)
16. Bossio R, Marcaccini S, Pepino R, Torroba T (1999) Studies on isocyanides and related compounds. A facile synthesis of substituted 3-cyano-2-methoxy-3- phenylpyrroles. Heterocycles 50:463-467. doi:10.1002/chin. 199924120
17. D'Souza DM, Mueller TJJ (2007) Multi-component syntheses of heterocycles by transition metal catalysis. Chem Soc Rev 36:1095-1108. doi:10.1039/b608235c
18. Isambert N, Lavilla R (2008) Heterocycles as key substrates in multicomponent reactions: the fast lane towards molecular complexity. Chem Eur J 14:8444-8454. doi:10.1002/chem.200800473
19. Arndtsen BA (2009) Metal-catalyzed one-step synthesis: towards direct alternatives to multistep heterocycle and amino acid derivative formation. Chem Eur J 15:302-313. doi:10.1002/chem. 200800767
20. Sunderhaus JD, Martin SF (2009) Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds. Chem Eur J 15:1300-1308. doi:10.1002/chem.200802140
21. Ramón DJ, Yus M (2005) Asymmetric multicomponent reactions (AMCRs): the new frontier. Angew Chem Int Ed 44:1602-1634. doi:10.1002/anie. 200460548
22. Lue P, Greenhill JV (1997) Enaminones in heterocyclic synthesis. Adv Heterocycl Chem 67:207-215
23. Elassar AA, El-Khair AA (2003) Recent developments in the chemistry of enaminones. Tetrahedron 59:8463-8480. doi:10. 1016/S0040-4020 (03) 01201-8 (Pubitemid 37220045)
24. Stanovnik B, Svete J (2004) Synthesis of heterocycles from alkyl 3-(dimethylamino) propenoates and related enaminones. Chem Rev 104:2433-2480. doi:10.1021/cr020093y
25. Erian AW, Sherif SM (1999) The chemistry of thiocyanic esters. Tetrahedron 55:7957-8024. doi:10.1016/S0040-4020 (99) 00386-5 (Pubitemid 29278832)
26. Goel A, Mazur SJ, Fattah RJ, Hartman TL, Turpin JA, Huang M, Rice WG, Appella E, Inman JK (2002) Benzamide-based thiolcarbamates: a new class of HIV-1NCp7 inhibitors. Bioorg Med Chem Lett 12:767-770. doi:10.1016/S0960-894X (02) 00007-0 (Pubitemid 34164614)
27. Morf PF, Raimondi FH-G, Nothofer BH-G, Schnyder B, Yasuda JM, Wessels JM, Jung TA (2006) Dithiocarbamates: functional and versatile linkers for the formation of self-assembled monolayers. Langmuir 22:658-663. doi:10.1021/la052952u (Pubitemid 43164802)
28. Dunn AD, Rudorf W-D (1989) Carbon disulphide in organic chemistry. Ellis Horwood, Chichester, UK, pp 226-367
29. Azizi N, Aryanasab F, Torkiyan L, Ziyaei A, Saidi MR (2006) Onepot synthesis of dithiocarbamates accelerated in water. J Org Chem 71:3634-3635. doi:10.1021/jo060048g
30. Azizi N, Aryanasab F, Saidi MR (2006) Straightforward and highly efficient catalyst-free one-pot synthesis of dithiocarbamates under solvent-free conditions. Org Lett 8:5275-5277. doi:10.1021/ol0620141 (Pubitemid 44861546)
31. Alizadeh A, Zohreh N (2009) A novel multicomponent method for the synthesis of 2-thioxo-1, 3-thiazolidin-4-ones. Synlett 2146-2148 doi:10.1055/s-0029-1217548
32. Han F, Ge Z, Cheng T, Li R (2009) Novel one-pot, four-component synthesis of 3-lkyldithiocarbonyloxazolidines from aminoethanols, ketones, carbon disulfide, and halides. Synlett 648-650 doi:10.1055/s-0028-1087918
33. Ziyaei Halimehjani A, Maleki H, Saidi MR (2009) Regiospecific iodocyclization of S-allyl dithiocarbamates: synthesis of 2-imino-1, 3-dithiolane and 2-iminium-1, 3-dithiolane derivatives. Tetrahedron Lett 50:2747-2749. doi:10.1016/j.tetlet.2009.03.127
34. Karpov AS, Müller TJJ (2003) Straightforward novel one-pot enaminone and pyrimidine syntheses by coupling-addition-cyclocondensation sequences. Synthesis 2815-2826 doi:10.1055/s-2003-42480 (Pubitemid 38064669)
35. Yavari I, Hosain-Nia A (1994) Differential rates of NH proton exchange reactions of two isomeric enaminones. Mag Res Chem 30:413-414
36. Schwan AL, Warkentin J (1988) The reactions of simple dimethylallylamines with dimethyl acetylenedicarboxylate. Formation ofdimethylamino-2-allylmaleates via formal allyl transfer. Can J Chem 66:1686-1694. doi:10.1139/v88-273
37. Herbig K, Huisgen R, Huber H (1966) cis-trans-Isomerization of enamine β-carboxylic acid esters. Steric course of the amine addition to carboxylic acid esters of the acetylene series. Chem Ber 99:2526-2545
38. Huisgen R, Herbig K, Siegl A, Huber H (1966) cis-trans-Isomerization of enamine β-carboxylic acid esters. Steric course of the amine addition to carboxylic acid esters of the acetylene series. Chem Ber 99:2546-2555
39. Sokolyanskaya LW, Varilova Volkov AN, Trofimov BA (1981) Study of diacetylene derivatives addition of ammonium dithiocarbamates to diacetylene. Zh Org Khim 17:2269-2272;
40. Chem Abst 96:103605n
41. Trofimov BA, Amosova SV, Ivanova NI, Tarasova OA, Alpert MLGV, Dmitrieva Sigalov MV (1986) New derivative of dithiocarbamic acid reaction of organyl dithiocarbamic acids. Zh Org Khim 22:2145-2149
42. Chem Abst 108:37214x
43. Sheldrick GM (2008) Bruker analytical X-ray-division. Madison, Wisconsin
44. Sheldrick GM (2008) A short history of SHELX. Acta Cryst A 64:112-122. doi:10.1107/S0108767307043930