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3-Nitroindoles Serving as N-Centered Nucleophiles for Aza-1,6-Michael Addition to para-Quinone Methides.

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.

SUBMITTER: Zhao JQ

PROVIDER: S-EPMC10384903 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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3-Nitroindoles Serving as N-Centered Nucleophiles for Aza-1,6-Michael Addition to para-Quinone Methides.

Zhao Jian-Qiang JQ Wang Wen-Jie WJ Zhou Shun S Xiao Qi-Lin QL Xue Xi-Sha XS Zhang Yan-Ping YP You Yong Y Wang Zhen-Hua ZH Yuan Wei-Cheng WC

Molecules (Basel, Switzerland) 20230720 14

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 electr ...[more]

PMID: 37513401

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