Highly Diastereoselective Synthesis of Polycyclic Indolines through Formal [4+2] Propargylic Cycloaddition of Indoles with Ethynyl Benzoxazinanones

• Published in: Chemistry, an Asian journal Vol. 15; no. 16; pp. 2462 - 2466
• Main Authors: Shao, Wen, Xu‐Xu, Qing‐Feng, You, Shu‐Li
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 17.08.2020
• Subjects: Chemical reactions; Chemistry; Cycloaddition; Heterocyclic compounds; Indoles; indoline; Organic compounds; propargylation; pyrrole; Quinoline; quinone methide; Stereoselectivity; Substrates; Synthesis

A formal [4+2] propargylic annulation of indoles and pyrrole with ethynyl benzoxazinanones was described. This protocol provides a concise synthesis of tetrahydro‐5H‐indolo[2,3‐b]quinolines and tetrahydro‐3H‐pyrrolo[3,2‐b]quinoline, the core structures of alkaloid frameworks, featuring excellent yie...