Abstract
Multicomponent reactions involving azines (phenanthridine or isoquinoline) and dimethyl acetylenedicarboxylate were undertaken in the presence of heterocyclic NH compounds (indole, 2-methyl indole, 3-methyl indole, carbazole and 3,6-dibromocarbazole) or 1,3-dicarbonyl compounds such as N,N′-dimethylbarbituric acid, 1,3-diethyl-2-thiobarbituric acid, acetylacetone, 1,3-diphenyl-1,3-propandione and cyclopentan-1,3-dione to generate enaminoesters in good yields.
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Acheson RM, Elmore NF (1978) Adv Chem (Kyoto) 23: 263
Adib M, Mollahosseini M, Yavari H, Sayahi MH, Bijanzadeh HR (2004) Simple one-pot three-component synthesis of 2-oxo-1,11b-dihydro-2H-pyrimidino [2,1-α] isoquinoline. Synthesis 6: 861–864. doi:10.1055/s-2004-815991
Adib M, Yavari H, Mollahosseini M (2004) Efficient one-pot synthesis of 2-oxo-1,9a-dihydro-2H-pyrido-[1,2-α] pyrimidine derivatives. Tetrahedron Lett 45: 1803–1805. doi:10.1016/j.tetlet.2003.12.082
Alba FJ, Bermudez A, Daban JR (2001) Green-light transilluminator for the detection without photodamage of proteins and DNA labeled with different fluorescent dyes. Electrophoresis 22:399403. doi:10.1002/1522-2683(200102)22:3<399::AID-ELPS399>3.0.CO;2-D
Bora U, Saikia A, Boruah RC (2003) A novel microwave-mediated one-pot synthesis of indolizines via a three-component reaction. Org Lett 5: 435–438. doi:10.1021/ol020238n
Cadogan JIG (1979) Organophosphorus reagents in organic synthesis. Academic Press, New York
Corbridge DEC (1995) Phosphorus: an outline of chemistry, biochemistry and uses, 5th edn, Chap 3. Elsevier, Amsterdam
Diaz JL, Miguel M, Lavilla R (2004) N-acylazinium salts: a new source of iminium ions for Ugi-Typ processes. J Org Chem 69: 3550–3553. doi:10.1021/jo049823n
Dömling A, Ugi I (2000) Multicomponent reaction with isocyanides. Angew Chem Int Ed 39:3168–3210. doi :10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U
Eliel El Wilen SH (1994) Stereochemistry of organic compounds. Wiley, New York, p 570
Engel R (1988) Synthesis of carbon–phosphorus bonds. CRC Press, Boca Raton
Evans P, Grigg R, York M (2000) Ring closing metathesis reactions of isoquinoline and β-carboline. Tetrahedron Lett 41: 3967–3970. doi:10.1016/S0040-4039(00)00489-5
Gilchrist TL (1985) Heterocyclic chemistry. Wiley, New York
Hassani Z, Islami MR, Sheibani H, Kalantari M, Saidi K (2006) A facile one-pot method for preparation of succinic esters containing several functional groups. Arkivoc i: 89–94
Hudson HR (1990) The chemistry of organophosphorus compounds. In: Hartly FR (eds) Primary, secondary and tertiary phosphates and heterocyclic organophosphorus (III) compounds, vol 1. Wiley, New York
Islami MR, Mollazehi F, Badiei A, Sheibani H (2006) Serendipitous synthesis of 1,4-benzothiazin derivatives using 2-[(2-aminophenyl) disulfanyl] aniline. Arkivoc xv: 25–29
Johanson AW (1966) Yield chemistry. Academic Press, London
(a) Juranovic I, Meic Z, Piantanida I, Tumir LM (2002) Interactions of phenanthridiumnucleobase conjugates with poly nucleotides in aqueous media. Chem Commun (Camb) 13:1432–1433. doi:10.1039/b202615e; (b) Tuite E, Norden B (1995) Intercalative interactions of ethidium dyes with triplex structures. Bioorg Med Chem 3:701–711. doi:10.1016/0968-0896(95)00061-K
Kalantari M, Islami MR, Hassani Z, Saidi K (2006) Synthesis of dimethyl 1-(trifluoromethyl)-3H-pyrrolizine-2,3-dicarboxylate using phosphorus compounds. Arkivoc x: 55–62
Katritzky AR, Rees CW (1984) Comprehensive heterocyclic chemistry. In: Bird CW, Cheeseman GWH (eds) vol 1. Pergamon Press, New York
Lynch MA, Duval O, Sukhanova A, Devy J, Mackay SP, Waigh RD et al (2001) Synthesis, biological activity and comparative analysis of DNA binding affinities and human DNA topoisomerase I inhibitory activities of novel 12-alkoxy-benzo[c] phenanthridinium salts. Bioorg Med Chem Lett 11: 2643–2646. doi:10.1016/S0960-894X(01)00520-0
Maghsoodlou MT, Habibi Khorassani SM, Rofouei MK, Adhamdoust SR, Nassiri M (2006) Triphenylphosphite as a good reagent for the diasteroselective synthesis of phosphonate esters. Arkivoc xii: 145–151
Maghsoodlou MT, Hazeri N, Habibi Khorassani SM, Rofouei MK, Rezaie M (2006) Diastereoselective synthesis of phosphonato esters by reaction between triphenylphosphite and acetylenic esters in the presence of NH-acid compounds. Arkivoc xiii: 117–123
Mangalagiu GC, Mangalagiu II, Olariu RI, Petrovanu MG (2000) 4-Methylpyridinium yeilds II: selective reactions of pyrimidinium yeilds with activated alkynes. Synthesis 14:2047–2050 doi:10.1055/s-2000-8731
Mullins ST, Sammes PG, West RM, Yahioglu G (1996) Preparation of some new intercalating europium (III) sensitizers. J Chem Soc, Perkin Trans 1: 75–81. doi:10.1039/p19960000075
Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS et al (2003) Strategies for via novel multicomponent reaction based on isocyanides and nucleophilic carbenes. Acc Chem Res 36: 899–907. doi:10.1021/ar020258p
Nair V, Sreekanth AR, Abhilash N, Biju AT, Rema Devi B, Menon RS et al (2003) Novel pyridine-catalyzed reaction of dimethyl acetylenedicarboxylate with aldehydes and n-tosylimines: efficient synthesis of 2-benzoylfumarates and 1-azadienes. Synthesis 12: 1895–1902. doi:10.1055/s-2003-41000
Nair V, Sreekanth AR, Abhilash NP, Biju ATN, Varma L, Viji S et al (2005) 1,4-Dipolar cycloaddition in organic synthesis: a facile route to isoquinoline fused heterocycles. Arkivoc xi: 178–188
(a) The Merck Index (1989) An Encyclopedia of Chemicals, Drugs, and Biologicals, 11th edn. Merck and CO., INC., p 6973 (b) Le TN, Gang SG, Cho WJ (2004) A facile synthesis of benzo[c]phenanthridine alkaloids: oxynitidine and oxysanguinarine using lithiated toluamide-benzonitrile cycloaddition. Tetrahedron Lett 42:2763-2766 (c). Geen GR, Mann IS, Mullane MV (1998) A Versatile synthesis of fully aromatic benezo[c]phenanthridine alkaloids. Tetrahedron 54:9875–9894
Teimouri MB, Bazhrang R (2005) Synthesis of new stable crystalline zwitterionic products from the reaction of 1-methylimidazole, acetylenic esters and strong cyclic CH-acids. J Chem Res 50–53
(a) Weber L, Illgen K, Almstetter M (1999) Discovery of new multi-component reactions with combinational methods. Synlett 366–374. doi:10.1055/s-1999–2612; (b) Bienayme H, Hulme C, Oddon G, Schmitt P (2000) Maximizing synthetic efficiency: multi-component transformations lead the way. Chem Eur J 6:3321–3329. doi:10.1002/1521–3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-A; (c) Ugi I, Domling A, Werner B (2000) Since 1995 the new chemistry of multi-component reactions and their libraries, including their heterocyclic chemistry. J Het Chem 37:647–658; (d) Ugi I, Heck S (2001) The multi-component reactions and their libraries for natural and preparative chemistry. Comb Chem High Throughput Screen 4:1–34
Wender PA, Haddy ST, Wright DL (1997) Towards the ideal synthesis. Chem Ind 765–769
(a) Whittaker J, Mcfadyen WD, Baguley BC, Murray V (2001) The interaction of DNA-targeted platinum phenanthridinium complexes with DNA in human cell. Anticancer Drug Des 16:81–89; (b) Whittaker J, Mcfadyen WD, Wickham G, Wakelin LPG, Murray V (1998) The interaction of DNA-targeted platinum phenanthridinium complexes with DNA. Nucleic Acids Res 26:3933–3939. doi:10.1093/nar/26.17.3933
Yavari I, Anary-Abbasinejad M, Alizadeh A (2002) A simple synthesis of stable 1,4-diionic pyridinium betaines. Monatsh Chem 133: 1331–1336. doi:10.1007/s007060200110
Yavari I, Nasiri F, Djahaniani H (2003) Triphenylphosphine catalized reaction between 1,3-dicarbonyl compounds and acetylenic esters. Phosphorus Sulfur Silicon Relat Elem 178: 2627–2638. doi:10.1080/714040976
Yavari I, Hossaini Z, Sabbaghan M (2006) A synthesis of pyrrolo [2,1, α] isoquinoline through the reaction of activated acetylenes and isoquinoline in the presence of ethyl bromopyruvate. Tetrahedron Lett 47: 6037–6040. doi:10.1016/j.tetlet.2006.06.113
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Nassiri, M., Maghsoodlou, M.T., Heydari, R. et al. Novel multicomponent reactions involving isoquinoline or phenanthridine and activated acetylenic ester in the presence of heterocyclic NH or 1,3-dicarbonyl compounds. Mol Divers 12, 111–117 (2008). https://doi.org/10.1007/s11030-008-9083-y
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DOI: https://doi.org/10.1007/s11030-008-9083-y