ISSN:
0170-2041
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Studies in the Field of Natural Product Chemistry, 801) - Cyclization Reactions and Claisen Rearrangements of 3-O-Substituted 1,3-Dihydroxy-10-methyl-9(10H)-acridinones - Synthesis of FuracridoneSelective etherification of the 3-hydroxy group of 1,3-dihydroxy-10-methyl-9(10H)-acridinone (1a) gave the ethers 1c-c. Cyclodehydration of 1c yielded a mixture of furacridone (2) and 3a in a ratio of about 6:1. Claisen rearrangement or cyclization of 1d and 1e in N,N-diethylaniline led to the isomeric mixtures 1i and 1h as well as 4 and 5 in ratios of 5:1 and 6:1, respectively, in favour of the C-4-substitution. By rearrangement of 1e in HMPT the linear 3b has been obtained.
Notes:
Durch selektive Veretherung der 3-Hydroxygruppe des 1,3-Dihydroxy-10-methyl-9(10H)-acridinons (1a) wurden die Ether 1c-e dargestellt. Cyclodehydratisierung von 1c gab ein ca. 6:1-Gemisch von Furacridon (2) und 3a. Claisen-Umlagerung oder Cyclisierung von 1d und 1e in N,N-Diethylanilin führten zu den Isomerengemischen 1i und 1h sowie 4 und 5 im Verhältnis von ca. 5:1 bzw. 6:1 zu Gunsten der C-4-Substitution. Die Umlagerung von 1e in HMPT gab das lineare 3b.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.198119810114
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