Tetrahedron Letters p. 4655 - 4658 (1997)
Update date:2022-09-26
Topics:
Moreaux, Veronique
Warren, Heidi
Williams, J. Michael
The cyclisation of the conjugate base of N-aryl-2,3:5,6-di-O-isopropylidene-4-O-methanesulfonyl-D- gulonamides gave the D-allonolactam acetals. Sodium methoxide-promoted cyclisation of 2,3:5,6-di-O-isopropylidene-4-O-methanesulfonyl-D-mannononitrile gave the D-talonolactim ether. Tetrazole formation without isolation of the intermediate azide was illustrated by the conversion of the aforementioned nitrile sulfonate into the D-talonotetrazole. Cyclic amidines were prepared from the lactam and lactim ether derivatives. The D-allono derivatives were also converted into D-ribono-1,4 lactam and amidine derivatives.
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