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Bortrifluorid-katalysierte Umsetzungen von 3-Amino-2H-azirinen mit Aminosäure-estern und Aminen

✍ Scribed by Martin Hugener; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1995
Tongue
German
Weight
888 KB
Volume
78
Category
Article
ISSN
0018-019X

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✦ Synopsis

Boron‐Trifluoride‐Catalyzed Reactions of 3‐Amino‐2__H__‐azirines with Amino‐acid Esters and Amines

After activation by protonation or complexation with BF~3~, 3‐amino‐2__H__‐azirines 1 react with the amino group of α‐amino‐acid esters 3 to give 3,6‐dihydro‐5‐aminopyrazin‐2(1__H__)‐ones 4 by ring enlargement (Scheme 2, Table 1). The configuration of 3 is retained in the products 4. With unsymmetrically substituted 1 (R^1^ ≠ R^2^), two diastereoisomers of 4 (cis and trans) are formed in a ratio of 1:1 to 2:1. With β‐amino‐acid esters 5 and 7, only openchain α‐amino‐imidamides 6 and 8, respectively, are formed, but none of the seven‐membered heterocycle (Scheme 3). Primary amines also react with BF~3~‐complexed 1 to yield α‐amino‐imidamides of type 9 (Scheme 4, Table 2). Compound 9b is characterized chemically by its transformation into crystalline derivatives 10 and 12 with 4‐nitrobenzoyl chloride and phenyl isothiocyanate, respectively (Scheme 5). The structure of 12 is established by X‐ray crystallography. Mechanisms for the reaction of activated 1 with amino groups are proposed in Schemes 6 and 7.

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