Journal
GREEN CHEMISTRY
Volume 24, Issue 14, Pages 5508-5513Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2gc01275h
Keywords
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Funding
- Fundamental Research Funds for the Central Universities
- Ocean University of China
- Qingdao National Laboratory for Marine Science and Technology [LMDBCXRC201902, LMDBCXRC201903]
- Taishan Scholar Program of Shandong Province [tsqn201909056, tsqn202103152]
- National Natural Science Foundation of China [22171251]
- Natural Science Foundation of Shandong Province [ZR2021QB033]
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This study developed a novel and efficient catalyst-free and oxidant-free synthesis method for highly substituted 5,6-dihydropyrazolo[5,1-a]isoquinolines. Different types of enamides and enamines, especially those derived from marketed drugs and bioactive molecules, are suitable substrates. The synthesis of a CB1 cannabinoid receptor antagonist using this methodology demonstrates its practicality for synthesizing valuable structural motifs.
A novel and efficient catalyst-free and oxidant-free tandem aza-Mannich/cyclization/aromatization reaction of C,N-cyclic azomethine imines with enamides has been developed. This practical one-step protocol enables a simple and environmentally friendly route toward the straightforward synthesis of highly substituted 5,6-dihydropyrazolo[5,1-a]isoquinolines. Different types of enamides and enamines, especially enamides derived from marketed drugs as well as bioactive molecules, are suitable substrates. CB1 cannabinoid receptor antagonist could be synthesized efficiently based on this methodology, illustrating that this would be a practical strategy to synthesize valuable structural motifs.
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