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ChemInform Abstract: Synthesis of Mesomeric Betaines, Quinoliziniumides, via Back-Donated 1,6-Cyclization.

✍ Scribed by Y. MATSUDA; K. KATOU; T. NISHIYORI; T. UEMURA; M. URAKAMI

Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Synthesis of Mesomeric Betaines, Quinoliziniumides, via Back-Donated 1,6-Cyclization.

-3-Aminopyridinium salts (I) react with polarized olefins to form the corresponding 3-aminopyridinium N-allylides (III). Thermolysis in xylene or acetic acid affords the back-donated 1,6-cyclization products (IV) and the 1,5-dipolar cyclization products. Acidic removal of the ethoxycarbonyl group yields the parent betain (VI). The pyridinium N-allylide (IX) takes another reaction course providing the indolizidine (X) in refluxing diphenyl ether.

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