4.8 Article

One-Step Synthesis of Hydropyrrolo[3,2-b]indoles via Cascade Reactions of Oxindole-Derived Nitrones with Allenoates

Journal

ORGANIC LETTERS
Volume 24, Issue 46, Pages 8493-8497

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03349

Keywords

-

Funding

  1. National Natural Science Foundation of China
  2. Science & Technology Department of Sichuan Province
  3. Innovation Team and Talents Cultivation Program of National Administration of Traditional Chinese Medicine
  4. Xinglin Scholar Research Promo-tion Project of Chengdu University of TCM
  5. China Postdoctoral Science Foundation
  6. [22001024]
  7. [82073998]
  8. [2022JDRC0045]
  9. [2021YJ0402]
  10. [2022JDRC0125]
  11. [ZYYCXTD-D-202209]

Ask authors/readers for more resources

In this study, a straightforward and efficient method for the synthesis of tetracyclic hydropyrrolo-[3,2-b]indole scaffolds was developed through a cascade reaction of oxindole-derived nitrones with allenoates. Multiple bond formations and cleavage could be achieved using a simple catalyst under mild conditions.
Hydropyrrolo[2,3-b]indole is a privileged indoline motif, while its analogue, hydropyrrolo[3,2-b]indole, has been much less explored. Herein, we developed a cascade reaction of oxindole-derived nitrones with allenoates, providing straightforward access to the tetracyclic hydropyrrolo-[3,2-b]indole scaffolds. Formation of multiple C-C/C-X bonds and cleavage could be achieved within one synthetic step using a simple catalyst (Gimeracil) under mild conditions. The reaction pathway may involve the generation of spiro-hydroazepinone as the key intermediate.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.8
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available