Synthesis, Inhaltsverzeichnis PAPER © Georg Thieme Verlag Stuttgart · New York Facile Synthesis of Highly Functionalized Stable Ketenimines via a Three-Component Reaction Abdolali Alizadeh*, Sadegh RostamniaDepartment of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, IranFax: +98(21)88006544; e-Mail: abdol_alizad@yahoo.com; e-Mail: aalizadeh@modares.ac.ir; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract It is shown that N-alkyl-substituted ketenimine derivatives can be efficiently prepared by the three-component coupling of electron-deficient alkynes, oximes, and isocyanides. The reaction is characterized by mild conditions, high selectivity, and tolerance to various functional groups. Yields are typically around 90%. Key words isocyanides - oximes - ketenimines - multicomponent reactions - zwitterions Volltext Referenzen References 1a Tidwell TT. Ketenes Wiley; New York: 1995. 1b Krow GR. Angew. Chem., Int. Ed. Engl. 1971, 10: 435 1c Barker MW. McHenry WE. The Chemistry of Ketenes, Allenes and Related Compounds Part 2: Wiley; New York: 1980. 2a Tidwell TT. Acc. Chem. Res. 1990, 23: 273 2b Chiang Y. Grant AS. Guo H.-X. Kresge AJ. Paine SW. J. Org. Chem. 1997, 62: 5363 2c Ye T. McKervey MA. Chem. Rev. 1994, 94: 1091 2d Birney DB. Xu X. Ham S. Huang X. J. Org. Chem. 1997, 62: 7114 2e Wagner BD. Arnold BR. Brown GS. Lusztyk J. J. Am. Chem. Soc. 1998, 120: 1827 3a Schmittel M. Steffen J.-P. Angel MAW. Engels B. Lennartz C. Hanrath M. Angew. Chem. Int. Ed. 1998, 37: 1562 3b Molina P. Alajarin M. Vidal A. Fenau-Dupont J. Declerq JP. J. Org. Chem. 1991, 56: 4008 3c Barbaro G. Battaglia A. Giorgianni P. Giacomini D. Tetrahedron 1993, 49: 4293 3d Weinreb SM. Lin X. Tetrahedron Lett. 2001, 42: 2631 3e Alcaide B. Martin-Cantalejo Y. Perez-Castells J. Sierra MA. J. Org. Chem. 1996, 61: 9156 3f Alajarin M. Vidal A. Tovar F. Arellano MCR. Tetrahedron: Asymmetry 2004, 15: 489 3g Calter MA. J. Org. Chem. 1996, 61: 8006 3h Taggi AE. Hafez AM. Wack H. Young B. Ferraris D. Lectka T. J. Am. Chem. Soc. 2002, 124: 6626 4a Ito M. Shirakawa E. Takaya H. Synlett 1996, 635 4b Qiao GGH. Andraos J. Wentrup C. J. Am. Chem. Soc. 1996, 118: 5634 4c Sung K. Tidwell TT. J. Am. Chem. Soc. 1998, 120: 3043 4d Allen AD. Tidwell TT. J. Org. Chem. 1999, 64: 266 4e Raspoet G. Nguyen MT. Kelly S. Hegarty AF. J. Org. Chem. 1998, 63: 9669 4f Frey J. Rappoport Z. J. Am. Chem. Soc. 1996, 118: 3994 4g Annette DA. Tidwell TT. J. Am. Chem. Soc. 1987, 109: 2774 4h Fu GC. Acc. Chem. Res. 2004, 37: 542 4i Acton AW. Allen AD. Antunes LM. Fedorov AV. Najafian K. Tidwell TT. Wagner BD. J. Am. Chem. Soc. 2002, 124: 13790 5a Fromont C. Masson S. Tetrahedron 1999, 55: 5405 5b Pietri N. Chiavassa T. Allouche A. Aycard JP. J. Phys. Chem. A 1997, 101: 1093 6a Allen AD. Cheng B. Fenwick MH. Givehchi B. Henry-Riyad H. Nikolaev VA. Shikhova EA. Tahmassebi D. Tidwell TT. Wang SL. J. Org. Chem. 2001, 66: 2611 6b Huang WW. Henry-Riyad H. Tidwell TT. J. Am. Chem. Soc. 1999, 121: 3939 6c Alajarin M. Vidal A. Ortin MM. Tetrahedron Lett. 2003, 44: 3027 6d Zora M. Sahpaz F. Ozarslan E. J. Org. Chem. 2003, 68: 1640 7a Alajarín M. Vidal A. Tovar F. Targets Heterocycl. Syst. 2000, 4: 293 7b Patai S. The Chemistry of Ketenes, Allenes and Related Compounds Wiley; New York: 1980. 7c See also ref. 1b. 8a Alcaide B. Casarrubios L. Domínguez G. Sierra MA. Curr. Org. Chem. 1998, 2: 551 8b Aumann R. Angew. Chem., Int. Ed. Engl. 1988, 27: 1456 9 Tietze LF. Chem. Rev. 1996, 96: 115 10 Ugi I. Angew. Chem., Int. Ed. Engl. 1982, 21: 810 11 Dömling A. Ugi I. Angew. Chem. Int. Ed. 2000, 39: 3169 12 Dömling A. Chem. Rev. 2006, 106: 17 13 Walborsky HM. Periasamy MP. In The Chemistry of Functional Groups Suppl. C: Patai S. Rappoport Z. Wiley; New York: 1983. Chap. 20. p.835 14 Marcaccini S. Torroba T. Org. Prep. Proced. Int. 1993, 25: 141 15 Shaabani A. Soleimani E. Khavasi HR. Hoffmann RD. Rodewald UC. Pöttgen R. Tetrahedron Lett. 2006, 47: 5493 16 Yavari I. Anary-Abbasinejad M. Alizadeh A. Hossaini Z. Tetrahedron 2003, 59: 1289 17 Yavari I. Zare H. Mohtat B. Mol. Diversity 2006, 10: 247 18 Yavari I. Nasiri F. Djahaniani H. Mol. Diversity 2004, 8: 431 19 Yavari I. Alizadeh A. Anary-Abbasinejad M. Bijanzadeh HR. Tetrahedron 2003, 59: 6083 20 Shaabani A. Teimouri MB. Arab-Ameri S. Tetrahedron Lett 2004, 45: 8409 21 Oakes TR. Donovan DJ. J. Org. Chem. 1973, 58: 1319 22a Alizadeh A. Rostamnia S. Zhu LG. Tetrahedron 2006, 62: 5641 22b Alizadeh A. Rostamnia S. Hu ML. Synlett 2006, 1592 22c Alizadeh A. Rostamnia S. Esmaili AA. Synthesis 2007, 709 22d Alizadeh A. Rostamnia S. Zohreh N. Oskueyan Q. Synlett 2007, 1610 22e Alizadeh A. Oskueyan Q. Rostamnia S. Synthesis 2007, 2637
