Meier, Hansruedi; Heimgartner, Heinz; Schmid, Hans (1977). Thermische und photochemisch induzierte intramolekulare, 1,3-dipolare Cycloadditionen von 4-Phenyl-3-(2-allylphenyl)-sydnon. Helvetica Chimica Acta, 60(3):1087-1090.
The title compound 9 was synthesised in the usual way, starting from 2-allylaniline and ethyl 2-bromo-2-phenylacetate, via the nitrosaminacid 8 (Scheme 2). 9 reacts at room temperature with its potential azomethinimine-function in an intramolecular [3+2]-cycloaddition to give the tricyclic compound 11 (Scheme 2). On irradiation, 9 yields the dihydro-3H-pyrazolo[2,3-a]indole 10 which probably arises by intramolecular [3+2]-cycloaddition of the corresponding intermediate nitrilimine.
The title compound 9 was synthesised in the usual way, starting from 2-allylaniline and ethyl 2-bromo-2-phenylacetate, via the nitrosaminacid 8 (Scheme 2). 9 reacts at room temperature with its potential azomethinimine-function in an intramolecular [3+2]-cycloaddition to give the tricyclic compound 11 (Scheme 2). On irradiation, 9 yields the dihydro-3H-pyrazolo[2,3-a]indole 10 which probably arises by intramolecular [3+2]-cycloaddition of the corresponding intermediate nitrilimine.
| Other titles: | Thermal and photochemically induced intramolecular 1,3-dipolar cycloaddition reactions of 4-phenyl-3-(2-allylphenyl)-sydnone |
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| Item Type: | Journal Article, refereed, original work |
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Scopus Subject Areas: | Physical Sciences > Catalysis
Life Sciences > Biochemistry Life Sciences > Drug Discovery Physical Sciences > Physical and Theoretical Chemistry Physical Sciences > Organic Chemistry Physical Sciences > Inorganic Chemistry |
| Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
| Language: | German |
| Date: | 1977 |
| Deposited On: | 29 Oct 2014 12:55 |
| Last Modified: | 24 Jan 2022 04:55 |
| Publisher: | Wiley-Blackwell Publishing, Inc. |
| ISSN: | 0018-019X |
| Funders: | Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung |
| OA Status: | Closed |
| Publisher DOI: | https://doi.org/10.1002/hlca.19770600333 |
| Project Information: |
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Meier, Hansruedi