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A simple synthesis of nitriles from aldoximes.

ABSTRACT: Easily synthesized aldoximes have been converted to the corresponding nitriles under very mild conditions by a simple reaction with 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) and DBU in CH(2)Cl(2), THF, or DMF. As an alternative reagent that eliminates the formation of hexamethylphosphoramide as a byproduct, use of 1H-benzotriazol-1-yl-4-methylbenzenesulfonate (Bt-OTs) and DBU was investigated. Reactions with this reagent also proceeded smoothly and in good yields, although in one case N-sulfonylation was observed. An attempt to gain mechanistic insight into the BOP-mediated reaction has been made using (31)P{(1)H} NMR. However, no phosphorus-bearing intermediate could be readily observed. Finally, the method has been applied to the synthesis of an antiviral 4'-cyano adenosine analogue from a commercial precursor using a single saccharide protecting group.

SUBMITTER: Singh MK

PROVIDER: S-EPMC2935138 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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A simple synthesis of nitriles from aldoximes.

Singh Manish K MK Lakshman Mahesh K MK

The Journal of organic chemistry 20090401 8

Easily synthesized aldoximes have been converted to the corresponding nitriles under very mild conditions by a simple reaction with 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) and DBU in CH(2)Cl(2), THF, or DMF. As an alternative reagent that eliminates the formation of hexamethylphosphoramide as a byproduct, use of 1H-benzotriazol-1-yl-4-methylbenzenesulfonate (Bt-OTs) and DBU was investigated. Reactions with this reagent also proceeded smoothly and in good y ...[more]

PMID: 19301882

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