First syntheses of natural products with the 2,7-dihydroxy-2H-1,4-benzoxazin-3(4H)-one skeleton

Autor:	Holger Hartenstein, Michael Kluge, Achim Hantschmann, Dieter Sicker
Rok vydání:	1995
Předmět:	chemistry.chemical_compound Acetic acid DIMBOA Glucoside chemistry Stereochemistry Organic Chemistry Acetal Hydrogen bromide Lactam Ether
Zdroj:	Journal of Heterocyclic Chemistry. 32:395-402
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570320204
Popis:	2,7-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one 11 (DHBOA) and 2,4,7-trihydroxy-2H-1,4-benzoxazin-3(4H)-one 14 (TRIBOA) representing aglucones of naturally occurring acetal glucoside type allelo chemicals found in Gramineae have been for the first time synthesized by two pathways both involving selective reductive cyclizations of appropriate 7-benzyloxy-2-nitrophenol derivatives as precursors. TRIBOA 14 and its bioactive naturally occurring 7-methyl ether DIMBOA have been found to undergo a hitherto unknown transformation to the corresponding 2,6-dibromo substituted lactam forms 20 and 21 in the presence of hydrogen bromide in acetic acid, which is of value in a better understanding of the possible mode of bioactivity.
Databáze:	OpenAIRE
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