Iron(III)-catalyzed tandem annulation of indolyl-substituted p -quinone methides with ynamides for the synthesis of cyclopenta[ b ]indoles.

Autor: Yu KY; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China. fanchunan@lzu.edu.cn., Ge XM; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China. fanchunan@lzu.edu.cn., Fan YJ; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China. fanchunan@lzu.edu.cn., Liu XT; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China. fanchunan@lzu.edu.cn., Yang X; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China. fanchunan@lzu.edu.cn., Yang YH; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China. fanchunan@lzu.edu.cn., Zhao XH; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China. fanchunan@lzu.edu.cn., An XT; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China. fanchunan@lzu.edu.cn., Fan CA; State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China. fanchunan@lzu.edu.cn.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2022 Aug 02; Vol. 58 (62), pp. 8710-8713. Date of Electronic Publication: 2022 Aug 02.
DOI: 10.1039/d2cc03252j
Abstrakt: The unique reactivity of indolyl-substituted p -QMs as a new type of two-carbon synthon has been explored for the first time in a novel iron(III)-catalyzed tandem annulation. This (2+2) annulation/retro-4π electrocyclization/imino-Nazarov cyclization cascade reaction is characterized by an unusual structural reconstruction of indolyl-substituted p -QMs, leading to an expeditious assembly of synthetically important functionalized cyclopenta[ b ]indoles.
Databáze: MEDLINE