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- Title
3-Nitroindoles Serving as N -Centered Nucleophiles for Aza-1,6-Michael Addition to para -Quinone Methides.
- Authors
Zhao, Jian-Qiang; Wang, Wen-Jie; Zhou, Shun; Xiao, Qi-Lin; Xue, Xi-Sha; Zhang, Yan-Ping; You, Yong; Wang, Zhen-Hua; Yuan, Wei-Cheng
- Abstract
An unprecedented N-alkylation of 3-nitroindoles with para-quinone methides was developed for the first time. Using potassium carbonate as the base, a wide range of structurally diverse N-diarylmethylindole derivatives were obtained with moderated to good yields via the protection group migration/aza-1,6-Michael addition sequences. The reaction process was also demonstrated by control experiments. Different from the previous advances where 3-nitrodoles served as electrophiles trapping by various nucleophiles, the reaction herein is featured that 3-nitrodoles is defined with latent N-centered nucleophiles to react with ortho-hydrophenyl p-QMs for construction of various N-diarylmethylindoles.
- Subjects
NUCLEOPHILES; QUINONE; POTASSIUM carbonate; ELECTROPHILES; INDOLE derivatives
- Publication
Molecules, 2023, Vol 28, Issue 14, p5529
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28145529