4.8 Article

Three-Component Domino Reactions for Selective Formation of Indeno[1,2-b]indole Derivatives

Journal

ORGANIC LETTERS
Volume 14, Issue 20, Pages 5210-5213

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol3023038

Keywords

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Funding

  1. NSFC [20928001, 21232004, 21072163, 21002083, 21102124]
  2. PAPD of Jiangsu Higher Education Institutions
  3. Robert A. Welch Foundation [D-1361]
  4. NIH [R21DA031860-01]

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Efficient three-component domino strategies for the synthesis of multifunctionalized tetracyclic indeno[1,2-b]indole derivatives with different substituted patterns have been established successfully. The first pathway involves a novel sequential methyl migration, aromatization, and esterification, while a second reaction in HOAc leads to compounds 6 with high syn diastereoselectivity. Both reactions showed attractive features including mild conditions, convenient one-pot operation, short reaction times of 15-32 min, and excellent regio- and/or stereoselectivity.

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