Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes
| Title: | Synthesis of new pyrazolo[1,2,3]triazines by cyclative cleavage of pyrazolyltriazenes |
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| Authors: | Nicolai Wippert, Martin Nieger, Claudine Herlan, Nicole Jung, Stefan Bräse |
| Source: | Beilstein Journal of Organic Chemistry, Vol 17, Iss 1, Pp 2773-2780 (2021) |
| Publisher Information: | Beilstein-Institut, 2021. |
| Publication Year: | 2021 |
| Collection: | LCC:Science LCC:Organic chemistry |
| Subject Terms: | cyclization, diazonium chemistry, pyrazoles, triazenes, triazines, Science, Organic chemistry, QD241-441 |
| More Details: | 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. |
| Document Type: | article |
| File Description: | electronic resource |
| Language: | English |
| ISSN: | 1860-5397 |
| Relation: | https://doaj.org/toc/1860-5397 |
| DOI: | 10.3762/bjoc.17.187 |
| Access URL: | https://doaj.org/article/50e41f45cc444177add2a48c383de361 |
| Accession Number: | edsdoj.50e41f45cc444177add2a48c383de361 |
| Database: | Directory of Open Access Journals |
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