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- W2061773002 abstract "Diaminocyclopropenyliumsalze (14a,b) reagieren in Dichloromethan mit den phosphorylierten Diazomethanen 15a-e in Gegenwart von Ethyl-diisopropylamin bzw. 1,5-Diazabicyclo[4.3.0]non-5-en spezifisch zu den 4,5-Diaminopyridazinen 16a-f. Aus dem Salz 14c und den Diazomethylverbindungen 15a,c,d sowie f-k in Dichlormethan im Beisein der bicyclischen Base bilden sich dagegen die 3,4-Diaminopyridazine 17a-i. In mechanistischer Hinsicht ist die Bildung intermediär auftretender (Diazomethyl)cyclopropene (14a,b + 15 → 18) bzw. (14c + 15 → 19) im Sinne der elektrophilen Diazoalkansubstitution zu interpretieren; weder 18, noch 19 lassen sich isolieren, sondern gehen eine rasche [1,5]-Cyclisierung zu den Betainen 20 bzw. 21 ein, die abschließend durch Öffnung der Brückenbindung zu den Pyridazinen 16 bzw. 17 isomerisieren. Diaminocyclopropenylium salts 14a,b react specifically with the phosphorylated diazomethanes 15a-e in dichloromethane in the presence of ethyl diisopropylamine and 1,5-diazabicyclo[4.3.0]non-5-ene respectively to the 4,5-diaminopyridazines 16a-f. In contrast to that the 3,4-diaminopyridazines 17a-i are formed in the reaction of the salt 14c with the diazomethyl compounds 15a,c,d such as f-k in dichloromethane in the presence of the bicyclic base. With regard to the reaction mechanism the formation of the intermediate diazomethyl cyclopropenes (14a,b + 15 → 18 or 14c + 15 → 19) has to be interpreted in the sense of an electrophilic diazoalkane substitution reaction; neither 18 nor 19 can be isolated but undergo a fast [1,5]-cyclization to the betaines 20 or 21, which finally isomerize to the pyridazines 16 or 17 by opening of the bridge bond." @default.
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- W2061773002 date "1986-03-01" @default.
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- W2061773002 title "Diaminopyridazine aus diaminocyclopropenyliumsalzen und (diazomethyl)- verbindungen" @default.
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- W2061773002 doi "https://doi.org/10.1002/jhet.5570230215" @default.
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