Expanding the substrate scope of ugi five-center, four-component reaction U-5C-4CR): Ketones as coupling partners for secondary amino acids

Molecular Diversity

Volumn 18, Issue 1, 2014, Pages 61-77

  Dawidowski, Maciej ^a   Sobczak, Sławomir ^a   Wilczek, Marcin ^b   Kulesza, Artur ^b   Turło, Jadwiga ^a  

^a MEDICAL UNIVERSITY OF WARSAW   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

Diastereoselectivity; Isocyanides; Molecular diversity; Multicomponent reactions; Ugi reaction

Indexed keywords

IMINO ACIDS; KETONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 84894057131     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-013-9488-0     Document Type: Article

References (29)

1. Biggs-Houck JE, Younai A, Shaw JT (2010) Recent advances in multicomponent reactions for diversity-oriented synthesis. Curr Opin Chem Biol 14:371-382. doi: 10.1016/j.cbpa.2010.03.003
2. Ugi I, Heck S (2001) The multicomponent reactions and their libraries for natural and preparative chemistry. Comb Chem High Throughput Screen 4:1-34. doi: 10.2174/1386207013331291
3. Hulme C, Gore V (2003) Multi-component reactions: emerging chemistry in drug discovery. From Xylocain to Crixivan. Curr Med Chem 10:51-80. doi: 10.2174/0929867033368600
4. Dömling A, Wang W, Wang K (2012) Chemistry and biology of multicomponent reactions. Chem Rev 112:3083-3135. doi: 10.1021/cr100233r
5. Kalinski C, Lemoine H, Schmidt J, Burdack C, Kolb J, Umkehrer M, Ross G (2008) Multicomponent reactions as a powerful tool for generic drug synthesis. Synthesis 24:4007-4011. doi: 10.1055/s-0028-1083239
6. Kalinski C, Umkehrer M, Weber L, Kolb J, Burdack C, Ross G (2010) On the industrial applications of MCRs: molecular diversity in drug discovery and generic drug synthesis. Mol Divers 14: 513-522. doi: 10.1007/s11030-010-9225-x
7. Ugi I, Meyr R, Fetzer U, Steinbrückner C (1959) Versuche mit Isonitrilen. Angew Chem 71:386-388. doi: 10.1002/ange.19590711110
8. Ugi I, Steinbrückner C (1960) Über ein neues Kondensations-Prinzip. Angew Chem 72:267-268. doi: 10.1002/ange.19600720709
9. Dömling A, Ugi I (2000) Multicomponent reactions with isocyanides. Angew Chem Int Ed 39:3168-3210. doi: 10.1002/1521-3773(20000915)39
10. Keating TA, Armstrong RW (1995) Molecular diversity via a convertible isocyanide in the Ugi four-component condensation. J Am Chem Soc 117:7842-7843. doi: 10.1021/ja00134a044
11. Lindhorst T, Bock H, Ugi I (1999) A new class of convertible isocyanides in the Ugi four-component reaction. Tetrahedron 55:7411-7420. doi: 10.1016/S0040-4020(99)00388-9
12. Pirrung MC, Ghorai S, Ibarra-Rivera TR (2009) Multicomponent reactions of convertible isonitriles. J Org Chem 74:4110-4117. doi: 10.1021/jo900414n
13. Hulme C, Ma L, Cherrier M-P, Romano JJ, Morton G, Duquenne C, Salvino J, Labaudiniere R (2000) Novel applications of convertible isonitriles for the synthesis of mono and bicyclic \gamma γ -lactams via a UDC strategy. Tetrahedron Lett 41:1883-1887. doi: 10.1016/S0040-4039(00)00052-6
14. Dömling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106:17-89. doi: 10.1021/cr0505728
15. Hulme C, Dietrich J (2009) Emerging molecular diversity from the intra-molecular Ugi reaction: iterative efficiency in medicinal chemistry. Mol Divers 13:195-207. doi: 10.1007/s11030-009-9111-6
16. Khoury K, Sinha MK, Nagashima T, Herdtweck E, Dömling A (2012) Efficient assembly of iminodicarboxamides by a "truly" four-component reaction. Angew Chem Int Ed 51:10280-10283. doi: 10.1002/anie.201205366
17. Bushkova E, Parchinsky V, Krasavin M (2010) Efficient entry into hydrazinopeptide-like structures via sequential Ugi reactions. Mol Divers 14:493-499. doi: 10.1007/s11030-009-9200-6
18. Liu N, Cao S, Wu J, Shen L, Yu J, Zhang J, Li H, Qian X (2010) A mild and efficient synthesis of monofluorinated \alpha α -lactam pseudopeptides via a novel dehydrofluorination of Ugi products. Mol Divers 14:501-506. doi: 10.1007/s11030-009-9209-x
19. Demharter A, Hörl W, Eberhardt H, Ugi I (1996) Synthesis of chiral 1,1 ′ -iminodicarboxylic acid derivatives from \alpha α -amino acids, aldehydes, isocyanides, and alcohols by the diastereoselective five-center-four-component reaction. Angew Chem Int Ed 35:173-175. doi: 10.1002/anie.199601731
20. Godet T, Bonvin Y, Vincent G, Merle D, Thozet A, Ciufolini MA (2004) Titanium catalysis in the Ugi reaction of alpha-amino acids with aromatic aldehydes. Org Lett 19:3281-3284. doi: 10.1021/ol048850x
21. Ugi I, Hörl W, Hanusch-Kompa C, Schmid T, Herdtweck E (1998) MCR 6: chiral 2,6-piperazinediones via Ugi reactions with \alpha α -amino acids, carbonyl compounds, isocyanides and alcohols. Heterocycles 47:965-975. doi: 10.3987/COM-97-S(N)108
22. Mandai H, Irie S, Mitsudo K, Suga S (2011) Studies on the synthesis of DMAP derivatives by diastereoselective Ugi reactions. Molecules 16:8815-8832. doi: 10.3390/molecules16108815
23. Liu H, Dömling A (2009) One-pot synthesis of highly functionalized seleno amino acid derivatives. Chem Biol Drug Des 74:302-308. doi: 10.1111/j.1747-0285.2009.00854.x
24. Sung K, Chen F-L, Chung M-J (2003) Application of MCR: facile one-pot diastereoselective syntheses of novel chiral alpha, alpha'-iminodiacetic acid analogues. Mol Divers 6:213-221. doi: 10.1023/B:MODI.0000006783.21086.0d
25. Szakonyi Z, Sillanpää R, Fülöp F (2010) Synthesis of conformationally constrained tricyclic \beta β -lactam enantiomers through Ugi four-center three-component reactions of a monoterpene-based \beta β -amino acid. Mol Divers 14:59-65. doi: 10.1007/s11030-009-9143-y
26. Park SJ, Keum G, Kang SB, Koh HY, Kim Y, Lee DH (1998) A facile synthesis of N-carbamoylmethyl- \alpha α -aminobutyrolactones by the Ugi multicomponent condensation reaction. Tetrahedron Lett 39:7109-7112. doi: 10.1016/S0040-4039(98)01509-3
27. Beck B, Srivastava S, Khoury K, Herdtweck E, Dömling A (2010) One-pot multicomponent synthesis of two novel thiolactone scaffolds. Mol Divers 14:479-491. doi: 10.1007/s11030-010-9249-2
28. Dawidowski M, Herold F, Wilczek M, Turło J, Chodkowski A, Gomółka A, Kleps J (2012) Synthesis of bicyclic 2,6-diketopiperazines via a three-step sequence involving an Ugi five-center, four-component reaction. Tetrahedron 68:8222-8230. doi: 10.1016/j.tet.2012.07. 064
29. Oldenziel OH, van Leusen D, van Leusen AM (1977) Chemistry of sulfonylmethyl isocyanides. 13. A general one-step synthesis of nitriles from ketones using tosylmethyl isocyanide. Introduction of a one-carbon unit. J Org Chem 42:3114-3118. doi: 10.1021/jo100004c