Due to their bifunctional character, alkylsulfamoyl chlorides are versatile units for the synthesis of heterocycles, polar sulfamates, and sulfonamides. In the last decade, synthetic methods of general preparative use have been developed, by means of which amine hydrochlorides, isocyanates, aziridines or tertiary alcohols can be reacted with suitable sulfuric acid derivatives to give novel, variously substituted alkylsulfamoyl chlorides. These compounds can subsequently be converted either to previously unobtainable N-alkoxyalkyl-N-alkylsulfamoyl chlorides or to novel heterocycles of the type 1 H-2,1,3-benzothiadiazin-4-one-2,2-dioxide, 2H-1,2,6-thiadiazin-3-one-1,l-dioxide and 2H-1,2,4,6-thiatriazin-5-one-l,l-dioxide; these compounds are examples of interesting models which illustrate the relation between the structure and the action of the compound, and in some cases lead to highly selective, ecologically unobjectionable herbicides. On the other hand, the alkylsulfamoyl chlorides themselves can be N-acylated to give further 3-to 5-atom bifunctional synthesis units, with which novel heterocyclic syntheses can be carried out. Further uses of the alkylsulfamoyl chlorides include the preparation of biologically active sulfamates, and cycloaddition reactions of N-sulfonylamines prepared in situ.
After incubation of radioactive catecholoestrogen monomethyl ethers with rat liver slices the following well known metabolic pathways were observed: 1) demethylation, 2) 16alpha-hydroxylation, 3) oxidoreduction at C-atom 17, and 4) conjugation with glutathione, sulphuric acid and glucuronic acid. In addition, for the first time a further aromatic ortho-hydroxylation, leading to pyrogalloloestrogen derivatives, was detected. Thus, the incubation of 2-methoxyoestrone yielded 2,4-dihydroxyoestrone 2-methyl ether as the main metabolite of the lipophile fraction. Under the same conditions, 4-methoxyoestrone was converted to 2,4-dihydroxyoestrone 4-methyl ether and 2,4-dihydroxyoestradiol-17beta 4-methyl ether; these compounds were the quantitatively most important metabolites not only in the lipophile but also in the sulphate and glucuronide fractions. The identity of these new metabolic products was established by chromatography, microchemical reactions and recrystallisation to constant specific radioactivity.
Die 1-Phenanthrenon-Derivate 3 a und b werden durch Diels-Alder-Reaktion der Dehydroaromaten I I und b mit dem Tetrahydrobenzo[h]furan 2 dargestellt. Aus 3 sind durch Abwandlungcn des Ringes B eine Reihe von Ketonen zuganglich, die sich zum Aufbau funktionalisierter Ostrogene eignen diirften. Die Umsetzung der Cyclohexadien-l,2-diol-Abkommlinge 7s, b und 8 mit Dimethylsulfoxonium-methylid fuhrt unter HOR-Eliminierung zum 10,lOa-Cyclopropa-Derivat 15.Polycyclic Compounds, VI'J' Synthesis a d Reactiws of (6,7-Dimethoxy)-tetrn-, -hexaand etahydro-I-phenanthrenonesThe hexahydro-1-phenanthrenone derivatives 3a and bare synthesized by the Diels-Alder reaction between the dehydrobenzenes 1 a and b and the tetrahydrobenzo[h]furan 2. Chemical transformations of the ring B of 3 lead to some tricyclic ketones, which seem to be of interest for the synthesis of functionalized estrogcnes. The reaction of the cyclohexadicne-1.2-diol derivatives 7n, b and 8 with dimethylsulfoxonium-methylide leads under elimination of HOR to the I0,IOa-cyclopropa-derivative 15.Biund tricyclische Ketone sind wichtige Zwischenprodukte zur Darstellung von Ostrogenen, da auf diesem Weg der stereoselektive Aufbau des in Steroiden meist vorliegenden 13-Alkyl-trans-hydrindan-Systems moglich ist 4. '*'I.Im Zusammenhang mit unserer kiirzlich beschriebenen I . ** ') Einstufendarstellung von Hexahydrochrysenen mit D-Homo-18-nor-equilenin-Struktur aus 6-substituierten 1.2-
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