Abstract
An efficient synthesis of 6H-6-iminothiopyran-2,3-dicarboxylate and 1H-isothiochromene-3,4-dicarboxylate derivatives via one-pot reactions between acetylenic esters, aryl isothiocyanates and enaminones in dichloromethane at room temperature is described. The mild reaction condition, high yields and the new products are advantages of our method.
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Yamamoto Y, Kinpara K, Saigoku T, Takagishi H, Okuda S, Nishiyama H, Itoh K (2005) Cp * RuCl-catalyzed [2 + 2 + 2] cycloadditions of α, ω-diynes with electron-deficient carbon-heteroatom multiple bonds leading to heterocycles. J Am Chem Soc 127: 605–613. doi:10.1021/ja045694g
Szymanski W, Zwolinska M, Ostaszewski R (2007) Studies on the application of the Passerini reaction and enzymatic procedures to the synthesis of tripeptide mimetics. Tetrahedron 63: 7647–7653. doi:10.1016/j.tet.2007.05.044
Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L (2003) Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes. Acc Chem Res 36: 899–907. doi:10.1021/ar020258p
Domling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed Engl 39: 3169–3210. doi:10.1021/cr0505728
Ugi I (1982) From isocyanides via four-component condensations to antibiotic syntheses. Angew Chem Int Ed Engl 21: 810–819. doi:10.1002/1521-3773(20000915)39:18<3168:AID-NIE3168>3.0.CO;2-U
Rogier DJ Jr, Carter JS, Talley JJ (2001) Dihydrobenzopyrans, dihydrobenzothiopyrans, and tetrahydroquinolines for the treatment of COX-2-mediated disorders, WO 2001049675. Chem Abstr 135: 107252
Brown MJ, Carter PS, Fenwick AE, Fosberry AP, Hamprecht DW, Hibbs MJ, Arvest RL, Mensah L, Milner PH, O’Hanlon PJ, Pope AJ, Richardson CM, West A, Witty DR (2002) The antimicrobial natural product chuangxinmycin and Some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase. Bioorg Med Chem Lett 12: 3171–3174. doi:10.1016/S0960-894X(02)00604-2
Quaglia W, Pigini M, Piergentili A, Giannella M, Gentili F, Marucci G, Carrieri A, Carotti A, Poggesi E, Leonardi A, Melchiorre C (2002) Selectivity of 4-phenylchroman analogues for alpha(1)-adrenoreceptor subtypes. J Med Chem 45: 1633–1643. doi:10.1021/jm011066n
Van Vliet LA, Rodenhuis N, Dijkstra D, Wikstrom H, Pugsley TA, Serpa KA, Meltzer LT, Heffner TG, Wise LD, Lajiness ME, Huff RM, Svensson K, Sundell S, Lundmark M (2000) Synthesis and pharmacological evaluation of thiopyran analogues of the dopamine D 3 receptor-selective agonist (4aR,10bR)-(+)-trans-3,4,4a,10b-tetrahydro-4-n-propyl-2H,5H [1] benzopyrano[4,3-b]-1,4-oxazin-9-ol (PD 128907). J Med Chem 43: 2871–2882. doi:10.1021/jm0000113
Wang W, Li H, Wang J, Zu LS (2006) Enantioselective organocatalytic tandem Michael–Aldol reactions: one-pot synthesis of chiral thiochromenes. J Am Chem Soc 128: 10354–10355. doi:10.1021/ja063328m
Samuel R, Asokan CV (2001) Synthesis of substituted 2-iminothiopyrans from aryl ethylidene malononitriles. Indian J Chem Sect B 40: 834–836
Nedolya NA, Brandsma L (1998) Synthesis of derivatives of 2-imino-5,6-dihydro-2H-thiopyran from 1-heteroalkyl-1,3-butadienes and isothiocyanates. Tetrahedron Lett 39: 2631–2634. doi:10.1016/S0040-4039(97)86431-3
Nedolya NA, Brandsma L, Verkruijsse H, Trofimov BA (1998) 2-Iminothiopyrans from methylthiobutadiene and isothiocyanates. Chem Heterocycl Compd 34: 550–553. doi:10.1007/BF02290937
Yavari I, Hossaini Z, Sabbaghan M, Ghazanfarpour-Darjani M (2009) A one-pot synthesis of functionalized thiazoles from acid chlorides, secondary amines, ethyl bromopyruvate, and ammonium thiocyanate. Mol Divers 13: 295–300. doi:10.1007/s11030-009-9114-3
Yavari I, Hossaini Z, Souri S (2009) Diastereoselective synthesis of fused [1,3]thiazolo[1,3]oxazins and [1,3]oxazino[2,3-b][1,3]benzothiazoles. Mol Divers 13: 439–443. doi:10.1007/s11030-009-9128-x
Foroumadi A, Zamanian S, Samzadeh-Kermani A, Shafiee A (2009) One-pot synthesis of 4-hydroxy-3-phenyl-2h-pyrano[3,2-b]benzofuran-2-one derivatives. Synth Commun 39: 1722–1728. doi:10.1080/00397910802585886
Alizadeh BH, Ostad SN, Foroumadi A, Amini M, Dowlatabadi R, Navidpour L, Shafiee A (2008) Synthesis and cytotoxic activity of novel chromenes. Arkivok 13: 45–56. doi:08-3057DP
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Hamadi, H., Khoobi, M., Hossaini, Z. et al. Facile and efficient synthesis of functionalized iminothiopyran and isothiochromen via one-pot multicomponent reactions. Mol Divers 15, 35–40 (2011). https://doi.org/10.1007/s11030-010-9230-0
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DOI: https://doi.org/10.1007/s11030-010-9230-0