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2005
Amide formation
O 0325
Novel Synthesis of α-Amino Carboxamides and Their Related Compounds via
Sulfones Starting from 2,2-Disulfonyloxiranes. — Oxiranes (IV) react with
08- 059 α-Oxo
primary or secondary amines (V) by a double nucleophilic addition yielding the
α-amino carboxamides (VI) in high yields. The attack of amine to the intermediary
α-oxo sulfone proceeds much faster than its attack to the starting oxirane. This phenomen is utilized for synthesizing cyclic α-amino carboxamides like α-azalactams
(VIII). The free amino-group of the intermediary α-oxo-sulfone reacts intramolecularly
with the carbonyl part affording cyclic carboxamides (VIII). Similarly, related compounds such as (X) and (XII) are synthesized from reagents possessing two nucleophilic sites. — (MATSUMOTO, S.; ISHII, M.; KIMURA, K.; OGURA*, K.; Bull.
Chem. Soc. Jpn. 77 (2004) 10, 1897-1903; Dep. Appl. Chem., Fac. Eng., Chiba Univ.,
Inage, Chiba 263, Japan; Eng.) — H. Hoennerscheid
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