A versatile multi-component one-pot thiazole synthesis

Synlett

Volumn , Issue 3, 2000, Pages 424-426

  Heck, Stefan ^a   Dömling, Alexander ^a,b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b Biovertis AG   (Germany)

Author keywords

Combinatorial chemistry; Isocyanide; Multi component reaction; One pot synthesis; Thiazole; Thiocarboxylic acid

Indexed keywords

AMINE; CARBOXYLIC ACID DERIVATIVE; ISONITRILE DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0039944586     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. Belshaw, P.J.; Roy, R.S.; Kelleher, N.L.; Walsh, C.T. Chem. Biol. 1998, 5, 373. Videnov, G.; Kaiser, D.; Brooks, M.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 1506. Roy, R.S.; Kelleher, N.L.; Milne, J.C.; Walsh, C.T. Chem. Biol. 1999, 6, 305. Konz, D.; Marahiel, M.A. Chem. Biol. 1999, 6, R39.
2. Belshaw, P.J.; Roy, R.S.; Kelleher, N.L.; Walsh, C.T. Chem. Biol. 1998, 5, 373. Videnov, G.; Kaiser, D.; Brooks, M.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 1506. Roy, R.S.; Kelleher, N.L.; Milne, J.C.; Walsh, C.T. Chem. Biol. 1999, 6, 305. Konz, D.; Marahiel, M.A. Chem. Biol. 1999, 6, R39.
3. Belshaw, P.J.; Roy, R.S.; Kelleher, N.L.; Walsh, C.T. Chem. Biol. 1998, 5, 373. Videnov, G.; Kaiser, D.; Brooks, M.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 1506. Roy, R.S.; Kelleher, N.L.; Milne, J.C.; Walsh, C.T. Chem. Biol. 1999, 6, 305. Konz, D.; Marahiel, M.A. Chem. Biol. 1999, 6, R39.
4. Belshaw, P.J.; Roy, R.S.; Kelleher, N.L.; Walsh, C.T. Chem. Biol. 1998, 5, 373. Videnov, G.; Kaiser, D.; Brooks, M.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 1506. Roy, R.S.; Kelleher, N.L.; Milne, J.C.; Walsh, C.T. Chem. Biol. 1999, 6, 305. Konz, D.; Marahiel, M.A. Chem. Biol. 1999, 6, R39.
5. Pettit, G.R.; Kamano, Y.; Herald, C.L.; Tuinam, A.A.; Boettner, F.E.; Kizu, H.; Schmidt, J.M.; Baczynskyj, L.; Tomer, K.B.; Bontems, R.J. J. Am. Chem. Soc. 1987, 109, 6883.
6. Takita, T.; Muraoka, Y.; Fujii, A.; Itoh, H.; Umezawa, H. J. Antibiot. 1972, 25, 187.
7. Steinberg, D.A.; Bernan, V.S.; Mentenegro, D.A.; Abbanant, D.R.; Pearce, C.J.; Korshalla, J.D. J. Antibiot. 1994, 47, 887.
8. eg.: Dolastatin 10: Iraco, N.; Hamada, Y.; Shioiri, T.; Tetrahedron 1992, 48, 7251. Bistartramide C: Aguilar, E.; Meyers, A.I. Tetrahedron Lett. 1994, 35, 2473 and 2477.
9. eg.: Dolastatin 10: Iraco, N.; Hamada, Y.; Shioiri, T.; Tetrahedron 1992, 48, 7251. Bistartramide C: Aguilar, E.; Meyers, A.I. Tetrahedron Lett. 1994, 35, 2473 and 2477.
10. Hantzsch, A. Ann. Chem. 1888, 249, 1. Use of Hantzsch reaction in the synthesis of Dolastatin 3: Schmidt, U.; Utz, R.; Lieberknecht, A.; Griesser, H.; Potzolli, B.; Bahr, J.; Wagner, K.; Fischer, P. Synthesis 1987, 233.
11. Hantzsch, A. Ann. Chem. 1888, 249, 1. Use of Hantzsch reaction in the synthesis of Dolastatin 3: Schmidt, U.; Utz, R.; Lieberknecht, A.; Griesser, H.; Potzolli, B.; Bahr, J.; Wagner, K.; Fischer, P. Synthesis 1987, 233.
12. 2 as an oxidant: Boden, C.; Pattenden, G. Tetrahedron Lett. 1994, 35, 8271.
13. 2 as an oxidant: Boden, C.; Pattenden, G. Tetrahedron Lett. 1994, 35, 8271.
14. 2 as an oxidant: Boden, C.; Pattenden, G. Tetrahedron Lett. 1994, 35, 8271.
15. Ugi, I.; Dömling, A.; Hörl, W. Endeavour 1994, 18, 430. Armstrong, R.W.; Combs, A.P.; Tempest, P.A.; Brown, S.D.; Keating, T.A. Acc. Chem. Res. 1996, 29, 123. Ugi, I. J. Prakt. Chem. 1997, 339, 499. Dömling, A. Comb. Chem. & High Through. Screen. 1999, 1, 1.
16. Ugi, I.; Dömling, A.; Hörl, W. Endeavour 1994, 18, 430. Armstrong, R.W.; Combs, A.P.; Tempest, P.A.; Brown, S.D.; Keating, T.A. Acc. Chem. Res. 1996, 29, 123. Ugi, I. J. Prakt. Chem. 1997, 339, 499. Dömling, A. Comb. Chem. & High Through. Screen. 1999, 1, 1.
17. Ugi, I.; Dömling, A.; Hörl, W. Endeavour 1994, 18, 430. Armstrong, R.W.; Combs, A.P.; Tempest, P.A.; Brown, S.D.; Keating, T.A. Acc. Chem. Res. 1996, 29, 123. Ugi, I. J. Prakt. Chem. 1997, 339, 499. Dömling, A. Comb. Chem. & High Through. Screen. 1999, 1, 1.
18. Ugi, I.; Dömling, A.; Hörl, W. Endeavour 1994, 18, 430. Armstrong, R.W.; Combs, A.P.; Tempest, P.A.; Brown, S.D.; Keating, T.A. Acc. Chem. Res. 1996, 29, 123. Ugi, I. J. Prakt. Chem. 1997, 339, 499. Dömling, A. Comb. Chem. & High Through. Screen. 1999, 1, 1.
19. Whereas the number of products obtainable by a two-component reaction increases linearly with the number of starting materials the products obtainable by a multi-component reaction increases with the power of the dimension of the MCR.
20. Heck, S.; Herdtweck, E.; Dömling, A. unpublished.
21. Schöllkopf, U.; Porsch, H.; Lau, H.H. Liebigs Ann. Chem. 1979, 95.
22. Yamashiro, D.; Li, C.H. Int. J. Peptide Protein Res. 1988, 31, 322.
23. 14 the cyclic imines were prepared as described in literature.
24. Dömling, A.; Ugi, I. Tetrahedron 1995, 49, 9495.
25. Martens, J.; Offermann, H.; Scherberich, P. Angew. Chem. Int. Ed. Engl. 1981, 20, 668.
26. 3): 22.5, 27.3, 52.5, 55.7, 73.8, 117.5, 128.0, 133.4, 136.2, 172.3, 198.9.
27. 3), 63.2 (CH), 126.1 (CH), 127.0 (CH), 128.4 (CH), 128.6 (CH), 137.0 (Cq), 145.9 (Cq), 161.6 (Cq), 168.5 (Cq), 171.9 (Cq).
28. 2), 88.7 (CH), 131.0 (CH), 145.4 (Cq), 161.8 (Cq), 169.7 (Cq), 170.3 (Cq).