ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Condensed Isoquinolines, VI. Reactions of 3-Oxo- and 3-Thioxo-2.3-dihydro-s-triazolo[3.4-a]isoquinolineAlkylation of 3-oxo-2.3-dihydro-s-triazolo[3.4-a]isoquinoline (1) with diazomethane leads to the N-methyl derivative 2 whereas the 3-thioxo compound 9 reacts with diazomethane or dimethyl sulfate to give the N-methyl and the S-methyl derivative. The latter is selectively oxidized to the sulfone 7 under acidic conditions and 9 is transformed into the disulfide 11 under basic conditions. α.ω-Dibromoalkanes (Br[CH2]nBr) react with 9. not depending on n, to give cyclic onium bromides 12, n = 2; n = 3, or (and) the substitution products 13, n = 2; n = 3, 14, n = 2; n = 4, and 15, n = 4; n = 5; n = 6. Their structures are assigned with the help of n.m.r and i.r. spectra.
Notes:
Die Alkylierung des 3-Oxo-2.3-dihydro-s-triazolo[3.4-a]isochinolins (1) mit Diazomethan führt zum N-Methyl-Derivat 2, während die 3-Thioxo-Verbindung 9 mit Diazomethan oder Dimethylsulfat das N-Methyl- und das S-Methyl-Derivat liefert. Letzteres wird unter sauren Bedingungen selektiv zum Sulfon 7 oxydiert und 9 unter basischen Bedingungen in das Disulfid 11 übergeführt. α.ω-Dibrom-alkane (Br[CH2]nBr) reagieren mit 9, unabhängig von n, zu cyclischen Oniumbromiden 12, n = 2; n = 3 oder (und) den Substitutionsprodukten 13, n = 2; n = 3; 14, n = 2; n = 4, und 15, n = 4; n = 5; n = 6, deren Strukturen mit Hilfe der NMR- und IR-Spektren gesichert werden.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19711041225
