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200517.fm Page 60 Friday, March 18, 2005 2:52 PM
2005
C-C bond formation
O 0282
Azole-N-acetonitriles as Carbonyl Synthons: A One-Pot Preparation of HeteroAmides from Halides. — The reaction of heterocyclic chlorides, e.g. (I) and
17- 057 aryl
(VII), with title azole-N-acetonitriles (II) proceeds with base-mediated SNAr substitution reaction followed by oxidation by an added peroxide. The generated acylated
azoles smoothly undergo reaction with in situ formed ammonia or an added amine to
finally afford the corresponding amides, e.g. (IV), (VI) or (VIII). Thus, the azole-N-acetonitriles serve as carbonyl synthons in the presented reaction. — (ZHANG, Z.;
YIN, Z.; KADOW, J. F.; MEANWELL, N. A.; WANG*, T.; Synlett 2004, 13,
2323-2326; Dep. Chem., Bristol-Myers Squibb Pharm. Res. Inst., Wallingford,
CT 06492, USA; Eng.) — Mischke
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