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Titolo:
FIRST SYNTHESES OF NATURAL-PRODUCTS WITH THE 2,7-DIHYDROXY-2H-1,4-BENZOXAZIN-3(4H)-ONE SKELETON
Autore:
KLUGE M; HARTENSTEIN H; HANTSCHMANN A; SICKER D;
Indirizzi:
UNIV LEIPZIG,INST ORGAN CHEM,TALSTR 35 D-04103 LEIPZIG GERMANY
Titolo Testata:
Journal of heterocyclic chemistry
fascicolo: 2, volume: 32, anno: 1995,
pagine: 395 - 402
SICI:
0022-152X(1995)32:2<395:FSONWT>2.0.ZU;2-6
Fonte:
ISI
Lingua:
ENG
Soggetto:
CYCLIC HYDROXAMIC ACIDS; LIQUID-CHROMATOGRAPHY; BENZOXAZOLINONE; GRAMINEAE; REDUCTION; LACTAMS; MAIZE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
31
Recensione:
Indirizzi per estratti:
Citazione:
M. Kluge et al., "FIRST SYNTHESES OF NATURAL-PRODUCTS WITH THE 2,7-DIHYDROXY-2H-1,4-BENZOXAZIN-3(4H)-ONE SKELETON", Journal of heterocyclic chemistry, 32(2), 1995, pp. 395-402

Abstract

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 ofnaturally occurring acetal glucoside type allelo chemicals found in Gramineae have been for the first time synthesized by two pathways bothinvolving 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 ahitherto 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.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 11/07/20 alle ore 19:48:47