Studies on Fluorinated Pyrimidines. IV. Stereochemistry of 6-Alkoxy-5-fluoro-5, 6-dihydrouracils and 5-Alkoxycarbonyl-5-fluoro-6-substituted-5, 6-dihydrouracils

Studies on Fluorinated Pyrimidines. IV. Stereochemistry of 6-Alkoxy-5-fluoro-5, 6-dihydrouracils and 5-Alkoxycarbonyl-5-fluoro-6-substituted-5, 6-dihydrouracils

Both cis (6) and trans (7) isomers of 6-alkoxy-5-fluoro-5, 6-dihydrouracils were prepared by catalytic hydrogenolysis of t-6-alkoxy-r-5-halogeno-5-fluoro-5, 6-dihydrouracils (4 and 5). The structures were estimated by comparing coupling constants (JH6F) in the proton magnetic resonance (PMR) spectra...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1982/07/25, Vol.30(7), pp.2333-2341
Hauptverfasser: MIYASHITA, OSAMU, KASAHARA, TOSHIHIKO, MATSUMURA, KOICHI, SHIMADZU, HIROSHI, TAKAMOTO, MASAYUKI, HASHIMOTO, NAOTO
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single-crystal X-ray analysis
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container_end_page 2341
container_issue 7
container_start_page 2333
container_title Chemical & pharmaceutical bulletin
container_volume 30
creator MIYASHITA, OSAMU
KASAHARA, TOSHIHIKO
MATSUMURA, KOICHI
SHIMADZU, HIROSHI
TAKAMOTO, MASAYUKI
HASHIMOTO, NAOTO
description Both cis (6) and trans (7) isomers of 6-alkoxy-5-fluoro-5, 6-dihydrouracils were prepared by catalytic hydrogenolysis of t-6-alkoxy-r-5-halogeno-5-fluoro-5, 6-dihydrouracils (4 and 5). The structures were estimated by comparing coupling constants (JH6F) in the proton magnetic resonance (PMR) spectra and confirmed by a single-crystal X-ray analysis of cis-6-ethoxy-5-fluoro-5, 6-dihydrouracil (6a). The stereochemistry of 6-alkoxy-5-alkoxycarbonyl-5-fluoro-5, 6-dihydrouracils (11-13) was clarified similarly on the basis of the PMR data. The chemical behavior of these compounds in acidic and basic media was examined.
doi_str_mv 10.1248/cpb.30.2333
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source J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry
subjects single-crystal X-ray analysis
title Studies on Fluorinated Pyrimidines. IV. Stereochemistry of 6-Alkoxy-5-fluoro-5, 6-dihydrouracils and 5-Alkoxycarbonyl-5-fluoro-6-substituted-5, 6-dihydrouracils
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