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Organic letters

New synthetic path to 2,2'-bipyridine-5,5'-dicarbaldehyde and its use in the [3+3] cyclocondensation with trans-1,2-diaminocyclohexane.


PMID 18027964

Abstract

2,2'-Bipyridine-5,5'-dicarbaldehyde has been prepared in two steps by enamination of 5,5'-dimethyl-2,2'-bipyridine with Bredereck's reagent, and subsequent oxidative cleavage of the enamine groups with sodium periodate. On condensation of this dialdehyde with enantiomerically pure trans-1,2-diaminocyclohexane, the macrocyclic [3+3] hexa Schiff base has been obtained in excellent yield. Its reduction has given large macrocyclic hexaamine having three bipyridine units incorporated into the macrocycle structure.

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270016
(±)-trans-1,2-Diaminocyclohexane, 99%
C6H14N2