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Synthesis of spiro[1,4-benzothiazine-2,2′-pyrans] starting from methyl β-D-arabino-2-hexulopyranosonate

✍ Scribed by Jens Andersch; Dieter Sicker; Horst Wilde

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
359 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Dedicated to Professor Klaus Burger on the occasion of his 60th birthday Methyl β‐D‐arabono‐2‐hexulopyranosonate 1 has via the novel glycosyl donor 3 been transformed into the thiophenyl glycosides 4 and 5. Catalytic hydrogenation of the nitro compound 4 in alkaline solution led to spontaneous cyclization and deprotection to form the cyclic hydroxamic acid 7. The related lactams 8 and 9 were obtained from amine 5. The spiro[1,4‐benzothiazine‐2,2′‐pyrans] 7–9 are the first representatives of a novel class of heterocycles structurally related to bioactive natural products. As shown by the values for J~3′,4′~ and J~4′,5′~ the glycosides 4, 5 and 6 adopt a ^5^C~2~ conformation of the pyranoid ring whereas the 1,4‐benzothiazine system in 7–9 forces a conformational change into the ^2^C~5~ conformation.

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