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The Reaction of 3-(Dimethylamino)-2H-azirines with 2,3-Pyridinedicarboximide

✍ Scribed by Jean-Pierre Obrech; Peter Schönholzer; Christain Johannes Jenny; Roland Prewo; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1988
Tongue
German
Weight
512 KB
Volume
71
Category
Article
ISSN
0018-019X

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✦ Synopsis

Reaction of 2,2-dialkyl-3-(dimethylamino)-2H-azirines la and l b with 2.3-pyridinedicarboximide (4) in MeCN or DMF at room temperature yielded two regioisomeric tricyclic 1:l adducts, the azacyclols 11/12 and 16/17, respectively (Schemes 3 and 4 ) . The structure of 12 was established by X-ray crystallography. Methanolysis of 11/12 and 16/17 led to mixtures of methyl [4,4-dialkyl-S-(dimethylamino)-4H-imidazol-2-yl]pyridine carboxylates 13/14 and 18/19, respectively. The structure of compound 14 is closely related to that of the powerful herbicide 9 (Scheme 9 ) , i.e. the described reactions offer a new synthetic approach to this class of compounds. A mechanistic interpretation for the formation of regioisomeric 1 : 1 adducts as well as methyl (imidazol-2-y1)pyridine carboxylates is depicted in Scheme 5.

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The cell dimensions were obtained from 72 and 25 accurately centered reflections with 36" i 1281 < 42" and 0" < I2b' < 50", respectively.

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