Reaction between alkyl isocyanides and isopropylidene Meldrum’s acid in the presence of bidentate nucleophiles
Molecular Diversity - 2006
Tóm tắt
The reaction between alkyl isocyanides and isopropylidene Meldrum’s acid in the presence of 1,2-ethanediol leads to N
1-(alkyl)-2-(5,7-dioxo-1,4-dioxepane-6-yl)-2-methylpropanamides. 1,3-Propanediol or 1,4-butanediol produce hydroxyalkyl 1-(tert-butyl)-4,4-dimethyl-2,5-dioxo-3-pyrrolidinecarboxylates. When the reaction was performed in the presence of catechol, bis(2-hydroxyphenyl) 2-[2-(tert-butylamino)-1,1-dimethyl-2-oxoethyl]malonate was obtained. 2-Aminophenols react with alkyl isocyanides in the presence of isopropylidene Meldrum’s acid to produce 1-alkyl-N
3-(2-hydroxyaryl)-4,4-dimethyl-2,5-dioxo-3-pyrrolidinecarboxamides in good yields.
Từ khóa
Tài liệu tham khảo
McNab H. (1978) Meldrum’s acid, Chem. Soc. Rev., 7: 345–358
Chen B.C. (1991) Meldrum’s acid in organic synthesis, Heterocycles, 32: 529–597
(a) Yavari, I. and Habibi, A., An efficient synthesis of highly functionalized S-alkyl 1-alkyl-4,4-dimethyl-pyrrolidine-3-carbothioates, Phosphorus, Sulfur, Silicon, 178 (2003) 1733–1740; (b) Yavari, I., Anari-Abbasinejad, M., Alizadeh, A. and Habibi, A., Stereoselective synthesis of 1,5-diionic organophosphorus compounds, Phosphorus, Sulfur, Silicon, 177 (2002) 2523–2527; (c) Yavari, I. and Habibi, A., Synthesis of alkyl 1-(tert-butyl)-4,4-dimethyl-2,5-dioxo-3-pyrrolidinecarboxylates, Polish J. Chem., 78 (2004) 71–74; (d) Yavari, I. and Habibi, A., Reaction between alkyl isocyanides and isopropylidene meldrum’s acid in the presence of pyrrole or indoles, Synthesis, (2004) 989–991; (e) Yavari, I., Habibi, A. and Hosseini-Tabatabaei, M.R., Reaction between 5-isopropylidene-2,2-dimethyl-1,3-dioxane-4,6-dione and tert-butyl isocyanide in the presence of primary or secondary amines, Monatsh. Chem., 134 (2003) 1651–1658; (f) Yavari, I., Hosseini-Tabatabaei, M.R. and Habibi, A., New synthesis of alkyl 1-tert-butyl-4,4-dimethyl-2,5-dioxo-pyrrlidine-3-carboxylate and dialkyl 2-(1-tert-butylcarbamoyl-1-methyl-ethyl-malonate, Synthetic Commun., 33 (2003) 2709–2717
(a) Yavari, I., Moradi, L., Nasiri, F. and Djahaniani, H., Regioselective reaction of N1-benzyl-N2-(4-nitrophenyl)-ethanediamide and acetylenic esters in the presence of tert-butyl isocyanide, Mendeleev Commun., 15 (2005) 156–158; (b) Yavari, I., Nasiri, F. and Djahaniani, H., Synthesis and dynamic NMR study of ketenimines derived from tert-butyl isocyanide, alkyl 2-arylamino-2-oxo-acetates, and dialkyl acetylenedicarboxylates, Mol. Divers., 8 (2004) 431–435; (c) Mosslemin, M.H., Yavari, I., Anary-Abbasinejad, M. and Nateghi, M.R., Reaction between tert-butyl isocyanide and 1,1,1-trifluoro-4-arylbutan-2,4-diones. Synthesis of new furan derivatives, J. Fluor. Chem., 125 (2004) 1497–1500; (d) Yavari, I., Djahaniani, H., and Nassiri, F., A␣simple synthesis of highly functionalized 1-azabutadienes and ketenimines, Monatsh. Chem., 134 (2004) 543–548; (e) Yavari, I., Djahaniani, H. and Nassiri, F., A simple synthesis of highly functionalized ketenimines derived from N-aryl-2,2,2-trichloroacetamide, alkyl isocyanides, and dialkyl acetylenedicarboxylates, Collect. Czech. Chem. Commun., 69 (2004) 1499–1505; (f) Yavari, I., Djahaniani, H. and Nasiri, F., Synthesis of coumarines and 4H-chromenes through the reaction of tert-butyl isocyanide and dialkyl acetylenedicarboxylates in presence of 2-hydroxybenzaldehydes, Synthesis, (2004) 679–682
Ugi I. (1982) From isocyanides via four-component condensations to antibiotic syntheses, Angew. Chem. Int. Ed. Engl., 21: 810–812
Dömling, A., Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev., 106 (2006) 17–89; Dömling, A. and Ugi, I., Multicomponent reactions with isocyanides, Angew. Chem. Int. Ed. Eng., 39 (2000) 3169–3210; Marcaccini, S. and Torroba, T., The use of isocyanides in heterocyclic synthesis, Org. Prep. Proced. Int., 25 (1993) 141–172