Diethyl Azodicarboxylate-Promoted Oxidative [3 + 2] Cycloaddition for the Synthesis of Pyrrolo[2,1‑a]isoquinolines
A novel metal-free protocol for the effective and efficient construction of pyrrolo[2,1-a]isoquinolines via a diethyl azodicarboxylate (DEAD)-promoted oxidative [3 + 2] cycloaddition/aromatization tandem reaction is described. Instead of the reported two-component oxidation systems, DEAD, as the s...
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| Published in: | Journal of organic chemistry Vol. 86; no. 1; pp. 91 - 102 |
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| Main Authors: | , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
United States
American Chemical Society
01-01-2021
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| Online Access: | Get full text |
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| Summary: | A novel metal-free protocol for the effective and efficient construction of pyrrolo[2,1-a]isoquinolines via a diethyl azodicarboxylate (DEAD)-promoted oxidative [3 + 2] cycloaddition/aromatization tandem reaction is described. Instead of the reported two-component oxidation systems, DEAD, as the sole oxidant, could smoothly transfer the tertiary amines to azomethine ylides via oxidation-deprotonation tandem process. The reaction proceeded with a broad substrate scope, giving rise to products in moderate to good isolated yields. |
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| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/acs.joc.0c01567 |