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Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes

Wippert, Nicolai; Nieger, Martin; Herlan, Claudine; Jung, Nicole; Bräse, Stefan

Abstract:

We describe the synthesis of so far synthetically not accessible 3,6-substituted-4,6-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines as nitrogen-rich heterocycles. The target compounds were obtained in five steps, including an amidation and a cyclative cleavage reaction as key reaction steps. The introduction of two side chains allowed a variation of the pyrazolo[3,4-d][1,2,3]triazine core with commercially available building blocks, enabling the extension of the protocol to gain other derivatives straightforwardly. Attempts to synthesize 3,7-substituted-4,7-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines, the regioisomers of the successfully gained 3,6-substituted 4,6-dihydro-3H-pyrazolo[3,4-d][1,2,3]triazines, were not successful under similar conditions due to the higher stability of the triazene functionality in the regioisomeric precursors and thus, the failure of the removal of the protective group.


Verlagsausgabe §
DOI: 10.5445/IR/1000141086
Veröffentlicht am 13.12.2021
Originalveröffentlichung
DOI: 10.3762/bjoc.17.187
Scopus
Zitationen: 2
Web of Science
Zitationen: 1
Dimensions
Zitationen: 3
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2021
Sprache Englisch
Identifikator ISSN: 1860-5397
KITopen-ID: 1000141086
HGF-Programm 43.33.11 (POF IV, LK 01) Adaptive and Bioinstructive Materials Systems
Erschienen in Beilstein journal of organic chemistry
Verlag Beilstein-Institut
Band 17
Seiten 2773–2780
Vorab online veröffentlicht am 22.11.2021
Schlagwörter cyclization; diazonium chemistry; pyrazoles; triazenes; triazines
Nachgewiesen in Dimensions
Web of Science
Scopus
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