ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Condensed Isoquinolines, IV. Syntheses with 3-Bromo- and 3-Hydrazino-s-triazolo[3.4-a]isoquinoline3-Bromo-s-triazolo[3.4-a]isoquinoline (2) or the unsubstituted s-triazolo[3.4-a]isoquinoline react with butyl lithium to afford the 3-lithio compound 4, which is stable at -70° and decomposes like the MgBr-salt at room temperature with cleavage of the triazolo ring to form l-aminoisoquinoline. From 2 and anthranilic acid 13-oxo-13H-isoquino[1′.2′ : 3.4]-s-triazolo[5.1-b]quinazoline (13) is obtained. N-acyl derivatives of 3-hydrazino-s-triazolo[3.4-a]iso-quinoline (14) cannot be cyclocondensed. 14 reacts with ethyl pyruvate to give via hydrazone 19 11-oxo-10-methyl-11H-as-triazino[4′.3′ : 1.5]-s-triazolo[3.4-a]isoquinoline (20). The thermal decomposition of 3-azido-s-triazolo[3.4-a]isoquinoline (22) in aniline leads to the phenylazo-derivative 23.
Notes:
Aus 3-Brom-s-triazolo[3.4-a]isochinolin (2) oder dem unsubstituierten s-Triazolo[3.4-a]isochinolin und Butyllithium entsteht die bei -70° stabile 3-Lithium-Verbindung 4, die wie das MgBr-Salz 3 bei Raumtemperatur unter Spaltung des Triazolringes in 1-Amino-isochinolin übergeht. Aus 2 und Anthranilsäure wird 13-Oxo-13H-isochino[1′.2′ : 3.4]-s-triazolo[5.1-b]-chinazolin (13) bereitet. N-Acyl-Derivate von 3-Hydrazino-s-triazolo[3.4-a]isochinolin (14) lassen sich nicht cyclokondensieren. 14 liefert mit Brenztraubensäureester via Hydrazon 19 das 11-Oxo-10-methyl-1 1H-as-triazino[4′.3′:1.5]-s-triazolo[3.4-a]isochinolin (20). Der thermische Zerfall von 3-Azido-s-triazolo[3.4-a]isochinolin (22) in Anilin führt zum Benzolazo-Derivat 23.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19711041223
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