Synthesis of new stable crystalline zwitterionic products from the reactions of 1-methylimidazole, acetylenic esters and strong cyclic CH-acids

Journal of Chemical Research

Volumn , Issue 1, 2005, Pages 50-53

  Teimouri, Mohammad Bagher ^a   Bazhrang, Reihane ^a  

^a IRAN POLYMER AND PETROCHEMICAL INSTITUTE   (Iran)

Author keywords

1 methylimidazole; CH acids; Dialkyl acetylenedicarboxylate; Nitrogen betaines; Zwitterionic species

Indexed keywords

1 METHYLIMIDAZOLE; 1,3 INDANDIONE DERIVATIVE; 5 [2 (1 METHYL 1H IMIDAZOL 3 IUM 3 YL) 1,2 ETHOXYCARBONYLETHYL] 1,3 DIMETHYL 2,4,6 TRIOXOHEXAHYDROPYRIMIDIN 5 IDE; 5 [2 (1 METHYL 1H IMIDAZOL 3 IUM 3 YL) 1,2 ETHOXYCARBONYLETHYL] 1,3 DIOXOINDAN 2 IDE; 5 [2 (1 METHYL 1H IMIDAZOL 3 IUM 3 YL) 1,2 ETHOXYCARBONYLETHYL] 2,2 DIMETHYL 4,6 DIOXO 1,3 DIOXAN 5 IDE; 5 [2 (1 METHYL 1H IMIDAZOL 3 IUM 3 YL) 1,2 METHOXYCARBONYLETHYL] 1,3 DIMETHYL 2,4,6 TRIOXOHEXAHYDROPYRIMIDIN 5 IDE; 5 [2 (1 METHYL 1H IMIDAZOL 3 IUM 3 YL) 1,2 METHOXYCARBONYLETHYL] 1,3 DIOXOINDAN 2 IDE; 5 [2 (1 METHYL 1H IMIDAZOL 3 IUM 3 YL) 1,2 METHOXYCARBONYLETHYL] 2,2 DIMETHYL 4,6 DIOXO 1,3 DIOXAN 5 IDE; 5 [2 (1 METHYL 1H IMIDAZOL 3 IUM 3 YL) 1,2 METHOXYCARBONYLETHYL] 2,4 DIOXOTETRAHYDROFURAN 3 IDE; 5 [2 (1 METHYL 1H IMIDAZOL 3 IUM 3 YL) 1,2 METHOXYCARBONYLETHYL] 2,5 DIOXOCYCLOPENTAN 1 IDE; 5 [2 (1 METHYL 1H IMIDAZOL 3 IUM 3 YL) 1,2 METHOXYCARBONYLETHYL] 2,6 DIOXOCYCLOHEXAN 1 IDE; ACETYLENE DERIVATIVE; ACID; AMPHOLYTE; BETAINE; CYCLOHEXANE DERIVATIVE; CYCLOPENTANE 1,3 DIONE; CYCLOPENTANE DERIVATIVE; DICARBOXYLIC ACID; DIHYDRORESORCINOL; ESTER; IMIDAZOLE DERIVATIVE; MELDRUM ACID; TETRONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 17144397531     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. E. Winterfeldt, Angew. Chem., Int. Ed. Engl. 1967, 6, 423.
2. (a) A.W. Johnson and J.C. Tebby, J. Chem. Soc. 1961, 2126;
3. (b) J.C. Tebby, I.F. Wilson and D.V. Grifiths, J. Chem. Soc., Perkin Trans. 1 1979, 2133.
4. E. Winterfeldt, Chem. Ber. 1964, 97, 1952.
5. E. Winterfeldt, Chem. Ber. 1965, 98, 1581.
6. (a) R.M. Acheson, Adv. Heterocycl. Chem. 1963, 1, 125;
7. (b) R.M. Acheson and N.F. Elmore, Adv. Heterocycl. Chem. 1978, 23, 263.
8. A. Demoulin, H. Gorissen, A.M. Hesbain-Frisque and L. Ghosez, J. Am. Chem. Soc. 1975, 97, 4409.
9. D.H. Aue and D. Thomas, J. Org. Chem. 1975, 40, 2360.
10. A. Crabtree and A.W. Johnson, J. Chem. Soc. 1962, 1510.
11. (a) R.M. Acheson, M.W. Foxton, P.J. Abbott and K.R. Mills, J. Chem. Soc. C 1967, 882;
12. (b) R.M. Acheson, P.J. Abbott, M.W. Foxton, N.R. Raulins and G. E. Robinson, J. Chem. Soc., Perkin Trans, 1 1972, 2182.
13. (a) O. Diels, K. Alder, H. Winckler and E. Petersen, Liebigs Ann. Chem. 1932, 498, 1;
14. (b) R.M. Acheson and O.A. Taylor, J. Chem. Soc. 1960, 4600.
15. R.M. Acheson and A.O. Plunkett, J. Chem. Soc. 1964, 2676.
16. (a) R. Huisgen, M. Morikawa, K. Herbig and E. Brunn, Chem. Ber. 1967, 100, 1094;
17. (b) M. Adib, H. Yavari and M. Mollahosseini, Tetrahedron. Lett. 2004, 45, 1803.
18. (a) V. Nair, A.R. Sreekanth, A.T. Biju and N.P. Rath, Tetrahedron. Lett. 2003, 44, 729;
19. (b) V. Nair, A.R. Sreekanth and A.U. Vinod, Org. Lett. 2001, 3, 3495;
20. (c) V. Nair, A.R. Sreekanth and A.U. Vinod, Org. Lett. 2002, 4, 2807;
21. (d) C.-Q. Li and M. Shi, Org. Lett. 2003, 5, 4273.
22. V. Nair, A.R. Sreekanth, N. Abhilash, A.T. Biju, B, Remadevi, R.S. Menon, N.P. Rath and R. Srinivas, Synthesis 2003, 1895.
23. V. Nair, B. R. Devi, N. Vidya, R. S. Menon, N. Abhilash and N. P. Rath, Tetrahedron. Lett. 2004, 45, 3203.
24. P. Bamfiled, A. Crabtree and A.W. Johnson, J. Chem. Soc. 1965, 4355.
25. (a) A. Shaabani, M.B. Teimouri, I. Yavari, H. Norouzi Arasi and H. R. Bijanzadeh, J. Fluorine Chem. 2000, 103, 155;
26. (b) A. Shaabani, M.B. Teimouri and H.R. Bijanzadeh, J. Chem. Res. (S) 2002, 381.
27. (c) A. Shaabani, A. Bazgir and M.B. Teimouri, Phosphorus, Sulfur and Silicon 2002, 177, 833;
28. (d) A. Shaabani, M.B. Teimouri, P. Mirzaei and H.R. Bijanzadeh, J. Chem. Res. (S) 2003, 82.
29. M. Karplus, J. Am. Chem. Soc. 1963, 85, 2870.