Regiocontrolled synthesis of highly-functionalized fused imidazoles: a novel synthesis of second generation LFA-1 inhibitors
β Scribed by Rogelio P. Frutos; Michael Johnson
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 143 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
A new and reliable route to a new class of LFA-1 inhibitors such as (2) has been developed. A key aspect of this route is the transformation of amino amide 5 into iodide 3 in four steps. Iodide 3 is a key advanced intermediate used in the synthesis of all second-generation 1H-imidazo[1,2-a]imidazol-2-one LFA-1 inhibitors.
π SIMILAR VOLUMES
Compounds 6-13 were prepared starting from 1-(triphenlymethy1)-protected 1H-imidazoles 14 and 15 in several steps. Lithiation with BuLi in T H F followed by reaction with (triphcny1methoxy)acetaldehyde (16) afforded 17 and 18, respectively. 0-Methylation of 17 and 18 gave diethers 19 and 20, respect
l-Seleno-2-silylethene 1 undergoes stereoseleetive SnCl,-promoted [2+1] cycloaddition reactions with 2-phosphonoacrylates 2 in high yields; the resulting highly functionalized cyclopropanephosphonic acid ester products 3 are versatile starting materiak for biologically important compounds. 0 1997Els