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Ca(II)-Catalyzed Cascade Reaction of Tryptamines with Propargylic Alcohols: Temperature-Driven Ring Opening and Closing via the Allene Migration Pathway for the Synthesis of Pyrrolo[1,2‑a]indoles
- Kale, Ashok;
- Kwon, Su Jeong;
- Lee, Joohan;
- Lee, Jae Kyun;
- Lee, Kyeong
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11초록
A temperature-dependent cascade of reactions between tryptamines and propargylic alcohols was developed to achieve selective formation of pyrroloindoline and pyrrolo[1,2-a]indole heterocycles by Ca(II) catalysis. The cascade consists of electrophilic addition of allene at the C3 carbon of indole followed by intramolecular cyclization at 60 degrees C to yield pyrroloindolines. Furthermore, simultaneous 1,2-allene migration and pyrrolidine ring opening were followed by intramolecular cyclization via C-N bond formation at reflux temperature to obtain pyrrolo[1,2-a]indole scaffolds. A wide range of substrates, a clean reaction profile, scalability, and good to excellent yields are the advantages of this protocol.
키워드
Carbon; Tryptamine; Alcohol Derivative; Carbon; Tryptamine; Tryptamine Derivative; Article; Catalysis; Controlled Study; Cyclization; Drug Analysis; Drug Development; Electrophilicity; Ring Opening; Signal Transduction; Synthesis; Temperature; ANTIFUNGAL ACTIVITY; CYCLIZATION; ALKALOIDS
- 제목
- Ca(II)-Catalyzed Cascade Reaction of Tryptamines with Propargylic Alcohols: Temperature-Driven Ring Opening and Closing via the Allene Migration Pathway for the Synthesis of Pyrrolo[1,2‑a]indoles
- 저자
- Kale, Ashok; Kwon, Su Jeong; Lee, Joohan; Lee, Jae Kyun; Lee, Kyeong
- 발행일
- 2024-02
- 유형
- Article
- 저널명
- Organic Letters
- 권
- 26
- 호
- 6
- 페이지
- 1196 ~ 1200