Synthesis of tetrasubstituted imidazoles via α-(N-acyl-N-alkylamino)-β-ketoamides on Wang resin

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 751-754

  Zhang, Chengzhi ^a   Moran, Edmund J ^a   Woiwode, Thomas F ^a   Short, Kevin M ^a   Mjalli, Adnan M M ^a  

^a Ontogen Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE;

ARTICLE; DRUG BINDING; DRUG SYNTHESIS; TECHNIQUE;

EID: 0030059786     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02310-0     Document Type: Article

References (31)

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15. Other heterocycles have been prepared by this method: (a) Pyrroles: Bossio, R.; Marcaccini, S.; Pepino, R. Synthesis 1994, 765. (b) Oxazoles: Bossio, R.; Marcaccini, S.; Pepino, R. Liebigs Ann. Chem. 1991, 1107.
16. Other heterocycles have been prepared by this method: (a) Pyrroles: Bossio, R.; Marcaccini, S.; Pepino, R. Synthesis 1994, 765. (b) Oxazoles: Bossio, R.; Marcaccini, S.; Pepino, R. Liebigs Ann. Chem. 1991, 1107.
17. Rink , H. Tetrahedron Lett. 1987, 28, 3787.
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22. (b) For the synthesis of isocyanides on other polymers using TsCl-pyridine, see: Arshady, R.; Ugi, I. Polymer 1990, 31, 1164 and references therein and Arshady, R.; Zecca, M.; Corain, B. React. Polym. 1993, 20 147. The conditions in this paper are incompatible with Wang resin.
23. (b) For the synthesis of isocyanides on other polymers using TsCl-pyridine, see: Arshady, R.; Ugi, I. Polymer 1990, 31, 1164 and references therein and Arshady, R.; Zecca, M.; Corain, B. React. Polym. 1993, 20 147. The conditions in this paper are incompatible with Wang resin.
24. 1H NMR of compounds bound to solid support are usually very broad and uninformative. In this case quite reasonable linewidths could be achieved with a judicious combination of exponential, gaussian and sine bell apodisations.
25. When kept in a vacuum dessicator, these resins are stable for up to 6 months at 23°C.
26. Mjalli, A. M. M.; Sarshar, S.; Baiga, T. J. J. Am. Chem. Soc. 1995, submitted.
27. 1H NMR showed that the crude isolate contained unreacted linker as the sole impurity.
28. - : 516.
29. Arylglyoxals can be prepared from: (a) α-bromoketones: (i) Kornblum, N.; Powers, J.; Anderson, G. J.; Jones, W. J.; Larson, H. O.; Levand, O. and Weaver, W. J. Am. Chem. Soc. 1957, 79, 6562. Gunn, V. E. and Anselme, J. P. J. Org. Chem. 1977, 42, 754. (b) aromatic esters: Mikol, G. J.; Russell, G. A. Org. Syntheses, Coll. 1973, 5, 937.
30. Arylglyoxals can be prepared from: (a) α-bromoketones: (i) Kornblum, N.; Powers, J.; Anderson, G. J.; Jones, W. J.; Larson, H. O.; Levand, O. and Weaver, W. J. Am. Chem. Soc. 1957, 79, 6562. Gunn, V. E. and Anselme, J. P. J. Org. Chem. 1977, 42, 754. (b) aromatic esters: Mikol, G. J.; Russell, G. A. Org. Syntheses, Coll. 1973, 5, 937.
31. Arylglyoxals can be prepared from: (a) α-bromoketones: (i) Kornblum, N.; Powers, J.; Anderson, G. J.; Jones, W. J.; Larson, H. O.; Levand, O. and Weaver, W. J. Am. Chem. Soc. 1957, 79, 6562. Gunn, V. E. and Anselme, J. P. J. Org. Chem. 1977, 42, 754. (b) aromatic esters: Mikol, G. J.; Russell, G. A. Org. Syntheses, Coll. 1973, 5, 937.