One-pot synthesis of highly functionalized stable ketenimines by three-component reaction of cyclohexyl isocyanide, dialkyl acetylenedicarboxylates, and benzoyl hydrazones

Synthetic Communications

Volumn 39, Issue 3, 2009, Pages 544-551

  Anary Abbasinejad, Mohammad ^a   Ghanea, Fatemeh ^a   Anaraki Ardakani, Hossein ^b  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Acetylenic esters; Benzoyl hydrazones; Isocyanides; Ketenimines; NH acids; Three component reaction

Indexed keywords

ACETYLENEDICARBOXYLIC ACID DERIVATIVE; BENZOYL HYDRAZONE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYANIDE; CYCLOHEXYL ISOCYANIDE; HYDRAZONE DERIVATIVE; IMINE; KETENIMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; MULTICOMPONENT REACTION; NONHUMAN; PRODUCT RECOVERY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION OPTIMIZATION; SYNTHESIS;

EID: 61649091388     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802406711     Document Type: Article

References (35)

1. Ugi, I. From isocyanides via four-component condensations to antibiotic syntheses. Angew. Chem., Int. Ed. Eng. 1982, 21, 810.
2. Ugi, I.; Lohberger, S.; Karl, R. In Comprehensive Organic Synthesis; B. M. Trost, I. Fleming, (Eds.); Pergamon: Oxford, 1991; vol. 2, p. 1083.
3. Domling, A.; Ugi, I. Multicomponent reactions with isocyanides. Angew. Chem., Int. Ed. Eng. 2000, 39, 3169.
4. Reichen, W. Oxygen-, nitrogen-, and sulfur-substituted heteroallenes. Chem. Rev. 1978, 78, 569.
5. Motoyoshiya, J.; Teranishi, A.; Mikoshiba, R.; Yamamoto, I.; Gotoh, H. C-Phosphonoketenimines: Characterization, and synthetic application to heterocycles. J. Org. Chem. 1980, 45, 5385.
6. Ishida, M.; Minami, T.; Agawa, T. Synthetic application of methyl (phenylthio) ketene: Synthesis of vicinal-substituted cyclopentene derivaties. J. Org. Chem. 1979, 44, 2067.
7. Krow, G. Synthesis and reaction of ketenimines. Angew. Chem., Int. Ed. Eng. 1971, 10, 435.
8. (a) Tidwell, T. T. Ketenes; Wiley: New York, 1995;
9. (b) Barker, M. W.; McHenry, W. E. The Chemistry of Ketenes, Allenes, and Related Compounds, Part 2; Wiley: New York, 1980.
10. (a) Tidwell, T. T. Ketene chemistry: The second golden age. Acc. Chem. Res. 1990, 23, 273;
11. (b) Chiang, Y.; Grant, A. S.; Guo, H.-X.; Kresge, A. J.; Paine, S. W. Flash photolytic decarbonylation and ring-opening of 2-(N-(pentafluorophenyl) amino)-3-phenylcyclopropenone: Isomerization of the resulting ynamine to a ketenimine, hydration of the ketenimine, and hydrolysis of the enamine produced by ring-opening. J. Org Chem. 1997, 62, 5363;
12. (c) Ye, T.; McKervey, M. A. Organic Synthesis with α-diazo carbonyl compounds. Chem. Rev. 1994, 94, 1091;
13. (d) Birney, D. B.; Xu, X.; Ham, S.; Huang, X. Chemoselectivity in the reactions of acetylketene and acetimidoylketene: Confirmation of theoretical predictions. J. Org Chem. 1997, 62, 7114;
14. (e) Wagner, B. D.; Arnold, B. R.; Brown, G. S.; Lusztyk, J. Spectroscopy and absolute reactivity of ketenes in acetonitrile studied by laser flash photolysis with time-resolved infrared detection. J. Am. Chem. Soc. 1998, 120, 1827.
15. (a) Schmittel, M.; Steffen, J. P.; Angel, M. A. W.; Engels, B.; Lennartz, C.; Hanrath, M. Two novel thermal biradical cyclizations of enyne-ketenimines: Theory, experiment, and synthetic potential. Angew. Chem. Int. Ed. 1998, 37, 1562;
16. (b) Alajarin, M.; Vidal, A.; Tovar, F.; Arellano, M. C. R. Stereocontrolled synthesis of azeto[2,1-b] quinazolines bearing three stereocenters via the intramolecular [2+2] cycloaddition between ketenimines and imines. Tetrahedron: Asymmetry 2004, 15, 489;
17. (c) Calter, M. A. Catalytic, asymmetric dimerization of methylketene. J. Org. Chem. 1996, 61, 8006.
18. (a) Qiao, G. G. H.; Andraos, J.; Wentrup, C. Reactivity of ketenes in matrices: Direct observation of ketene-pyridine ylides. J. Am. Chem. Soc. 1996, 118, 5634;
19. (b) Sung, K.; Tidwell, T. T. Amination of ketene: A theoretical study. J. Am. Chem. Soc. 1998, 120, 3043;
20. (c) Annette, D. A.; Tidwell, T. T. Kinetics and mechanism of hydration of alkyl ketenes. J. Am. Chem. Soc. 1987, 109, 2774;
21. (d) Acton, A. W.; Allen, A. D.; Antunes, L. M.; Fedorov, A. V.; Najafian, K.; Tidwell, T. T.; Wagner, B. D. Amination of pyridylketenes: experimental and computational studies of strong amide enol stabilization by the 2-pyridyl group. J. Am. Chem. Soc. 2002, 124, 13790.
22. (a) Fromont, C.; Masson, S.; Reactivity of N-phenyl silylated ketenimines with electrophilic reagents. Tetrahedron 1999, 55, 5405;
23. (b) Pietri, N.; Chiavassa, T.; Allouche, A.; Aycard, J. P. IR structural identification of oxocumulene HCl complexes generated in cryogenic matrixes: The product-like transition state of the corresponding electrophilic addition. J. Phys. Chem. A. 1997, 101, 1093.
24. Shaabani, A.; Soleimani, E.; Khavasi, H. R.; Hoffmann, R. D.; Rodewald, U. C.; Pöttgen, R. An isocyanide-based three-component reaction: Synthesis of fully substituted N-alkyl-2-triphenylphosphoranylidene glutarimides. Tetrahedron Lett. 2006, 47, 5493.
25. Yavari, I.; Anary-Abbasinejad, M.; Alizadeh, A.; Hossaini, Z. A simple and efficient approach to the synthesis of highly functionalized fused benzochromenes. Tetrahedron 2003, 59, 1289.
26. Yavari, I.; Zare, H.; Mohtat, B. Three-component synthesis of dialkyl 2-(alkylimino-methylene)-3-(2,2,5-trimethyl-4,6-dioxo-1,3-dioxan-5-yl) -succinates. Mol. Diversity 2006, 10, 24.
27. Yavari, I.; Nasiri, F.; Djahaniani, H. Synthesis and dynamic NMR study of ketenimines derived from tert-butyl isocyanide, alkyl 2-arylamino-2-oxo-acetates, and dialkyl acetylenedicarboxylates. Mol. Diversity 2004, 8, 431.
28. Yavari, I.; Alizadeh, A.; Anary-Abbasinejad, M.; Bijanzadeh, H. R. Reaction between alkyl isocyanides and dibenzoylacetylene in the presence of strong NH-acids: Synthesis of highly functionalized aminofurans. Tetrahedron 2003, 59, 6083.
29. Shaabani, A.; Teimouri, M. B.; Arab-Ameri, S. A novel pseudo four-component reaction: Unexpected formation of densely functionalized pyrroles. Tetrahedron Lett. 2004, 45, 8409.
30. Anary-Abbasinejad, M.; Mosslemin, M. H.; Tahan, S.; Anaraki-Ardakani, H. Synthesis of unsaturated amidines by three component reaction of alkylisocyanides, dialkyl acetylenedicarboxylates, and aromatic amides. J. Chem. Res. 2006, 3, 170.
31. Anary-Abbasinejad, M.; Mosslemin, M. H.; Anaraki-Ardakani, H.; Tahan, S. Synthesis of unsaturated amidine derivatives by three component reaction of alkyl isocyanides, dialkyl acetylenedicarboxylates, and pyrrole or indole. J. Chem. Res. 2006, 5, 306.
32. Anary-Abbasinejad, M.; Anaraky-Ardakani, H.; Rastegari, F.; Hassanabadi, A. One-pot synthesis of functionalized keteneimins by three component reaction of isocyanides, dialkyl acetylenedicarboxylates, and 4-phenylaminocoumarin. J. Chem. Res. 2007, 10, 602.
33. Dömling, A. Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem. Rev. 2006, 106, 17.
34. Walborsky, H. M.; Periasamy, M. P. In The Chemistry of Functional Groups, Suppl. C; S. Patai, Z. Rappoport, (Eds.); Wiley: New York, 1983; Chap. 20, 835.
35. Marcaccini, S.; Torroba, T. Use of isocyanides in heterocyclic synthesis. Org. Prep. Proced. Int. 1993, 25, 141.