FORMATION OF 4a, 5-DIHYDRO-4a-HYDROXY-5-DEAZAFLAVINS IN THE REACTION OF 1, 5-DIHYDRO-5-DEAZAFLAVINS WITH m-CHLOROPERBENZOIC ACID AND THEIR PYRIMIDINE RING CONTRACTION WITH BASE

FORMATION OF 4a, 5-DIHYDRO-4a-HYDROXY-5-DEAZAFLAVINS IN THE REACTION OF 1, 5-DIHYDRO-5-DEAZAFLAVINS WITH m-CHLOROPERBENZOIC ACID AND THEIR PYRIMIDINE RING CONTRACTION WITH BASE

A new class of 4a, 5-dihydro-4a-hydroxy-5-deazaflavins, which are isosteric and isoelectronic with the flavin pseudobase, was synthesized by the reaction of 1, 5-dihydro-5-deazaflavins with m-chloroperbenzoic acid. The base catalyzed hydrolysis of the 4a, 5-dihydro-4a-hydroxy-5-deazaflavins was carr...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1984/09/25, Vol.32(9), pp.3761-3763
Hauptverfasser: Yoneda, Fumio, Tanaka, Kiyoshi, Sakuma, Yoshiharu, Yoshino, Hironori, Takamoto, Masayuki
Format: Artikel
Sprache:eng
Schlagworte:
3, 4-dihydro-3-hydroxyquinolin-2 (1H)-one
Chemistry
Condensed matter: structure, mechanical and thermal properties
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Organic compounds
Physics
Preparations and properties
Structure of solids and liquids
crystallography
Structure of specific crystalline solids
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Zusammenfassung:A new class of 4a, 5-dihydro-4a-hydroxy-5-deazaflavins, which are isosteric and isoelectronic with the flavin pseudobase, was synthesized by the reaction of 1, 5-dihydro-5-deazaflavins with m-chloroperbenzoic acid. The base catalyzed hydrolysis of the 4a, 5-dihydro-4a-hydroxy-5-deazaflavins was carried out to give the corresponding 9, 9a-dihydrooxazolo [4, 5-b] quinolin-2 (4H)-ones.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.32.3761