The Concept of Sequential Multicomponent Reactions: A Short Synthesis of Thiazolo- and Oxazolo[1,4]benzodiazepine-2,5-diones

Abstract

A new synthetic sequence including two sequential multicomponent reactions leading to a wide range of thiazolo- and oxazolo-annulated benzodiazepinediones is described. This strategy features simple one-pot operations under mild conditions in combination with a high degree of diversity, and can be realized based on commercially available or easily accessible starting materials.

Key words

Ugi reaction - multicomponent reactions - cyclization - heterocycles - imines - polycycles

• References

• 1a Koblish HK, Zhao S. Mol. Cancer Ther. 2006; 5: 160
• 1b Kuno F, Otoguro K, Shiomi K, Iwai Y, Omura S. J. Antibiot. 1996; 49: 742
• 1c Mohamed LW, El-Yamany MF. Arch. Pharm. Res. 2012; 35: 1369
• 2 Parks DJ, LaFrance LV, Calvo RR, Milkiewicz KL, Gupta V, Lattanze J, Ramachandren K, Carver TE, Petrella EC, Cummings MD, Maguire D, Grasberger BL, Lu T. Bioorg. Med. Chem. Lett. 2005; 15: 765
• 3 Kalinski C, Umkehrer M, Ross G, Kolb J, Burdack C, Hiller W. Tetrahedron Lett. 2006; 47: 3423
• 4 Smits G, Zemribo R. Synlett 2015; 26: 2272
• 5a Tempest P, Ma V, Thomas S, Hua Z, Kelly MG, Hulme C. Tetrahedron Lett. 2001; 42: 4959
• 5b Tempest P, Ma V, Kelly MG, Jones W, Hulme C. Tetrahedron Lett. 2001; 42: 4963
• 5c Kalinski C, Umkehrer M, Gonnard S, Jäger N, Ross G, Hiller W. Tetrahedron Lett. 2006; 47: 2041
• 5d Xu Z, De Moliner F, Cappelli AP, Hulme C. Org. Lett. 2013; 15: 2738
• 6a Ugi I. J. Prakt. Chem. 1997; 339: 499
• 6b Dömling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
• 7a Colombo M, Peretto I. Drug Discovery Today 2008; 13: 677
• 7b Slobbe P, Ruijter E, Orru RV. A. Med. Chem. Commun. 2012; 3: 1189
• 7c Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083
• 7d van der Heijden G, Ruijter E, Orru RV. A. Synlett 2013; 24: 666
• 7e Dömling A, Zarganes-Tzitzikas T. Org. Chem. Front. 2014; 1: 834
• 7f Hulme C, Ayaz M, Martinez-Ariza G, Medda F, Shaw A In Small Molecule Medicinal Chemistry: Strategies and Technologies . Czechtizky W, Hamley P. Wiley; Weinheim: 2015. Chap. 6
• 7g Gollner A. Synlett 2015; 26: 426
• 8a Dömling A. Chem. Rev. 2006; 106: 17
• 8b Huang Y, Dömling A In Isocyanide Chemistry: Applications in Synthesis and Material Science . Nenajdenko VG. Wiley-VCH; Weinheim: 2012. Chap. 12
• 9 Asinger F. Angew. Chem. 1956; 68: 376
• 10 Weigert WM, Offermanns H, Degussa PS. Angew. Chem., Int. Ed. Engl. 1975; 14: 330
• 11 Martens J, Offermanns H, Scherberich P. Angew. Chem., Int. Ed. Engl. 1981; 20: 668
• 12 Weber M, Jakob J, Martens J. Liebigs Ann. Chem. 1992; 1
• 13 Liu Z.-Q. Curr. Org. Synth. 2015; 12: 20
• 14a Ugi I, Meyer R, Fetzer U, Steinbrückner C. Angew. Chem. 1959; 71: 386
• 14b Ugi I. Angew. Chem., Int. Ed. Engl. 1962; 1: 8
• 14c Ugi I, Wischhöfer E. Chem. Ber. 1962; 95: 136

For selected examples, see:
• 15a Kintscher J, Martens J. Synthesis 1992; 837
• 15b Hatam M, Tehranfar D, Martens J. Synth. Commun. 1995; 25: 1677
• 15c Brockmeyer F, Kröger D, Stalling T, Schwäblein A, Martens J. Helv. Chim. Acta 2012; 95: 1857
• 16 Stalling T, Pauly J, Kröger D, Martens J. Tetrahedron 2015; 71: 8290
• 17 Kröger D, Schlüter T, Fischer M, Geibel I, Martens J. ACS Comb. Sci. 2015; 17: 202
• 18a Van Berkel SS, Bögels BG. M, Wijdeven MA, Westermann B, Rutjes FP. J. T. Eur. J. Org. Chem. 2012; 3543
• 18b Banfi L, Riva R, Basso A. Synlett 2010; 23
• 18c Brockmeyer F, van Gerven D, Saak W, Martens J. Synthesis 2014; 46: 1603
• 19 Fulmer GR, Miller AJ. M, Sherden NH, Gottlieb HE, Nudelman A, Stoltz BM, Bercaw JE, Goldberg KI. Organometallics 2010; 29: 2176
• 20 Guirado A, Zapata A, Gómez JL, Trabalón L, Gálvez J. Tetrahedron 1999; 55: 9631
• 21 Herman LW, Sharma W, Kronauge JF, Barbarics E, Herman LA, Piwnica-Worms D. J. Med. Chem. 1995; 38: 2955