General and efficient synthesis of 1,2-dihydropyrrolo[3,4-b]indol-3-ones via a formal [3 + 2] cycloaddition initiated by C

General and efficient synthesis of 1,2-dihydropyrrolo[3,4-b]indol-3-ones via a formal [3 + 2] cycloaddition initiated by C–H activation

Published:2020 Issue:24 Volume:7 Page:4057-4063
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Xing Siyang¹²³⁴⁵^ORCID,Guo Junsuo¹²³⁴⁵,Wang Yuhan¹²³⁴⁵,Wang Chenyu¹²³⁴⁵,Wang Kui¹²³⁴⁵^ORCID,Zhu Bolin¹²³⁴⁵^ORCID

Affiliation:

1. Tianjin Key Laboratory of Structure and Performance for Functional Molecules

2. College of Chemistry

3. Tianjin Normal University

4. Tianjin 300387

5. People's Republic of China

Abstract

A [Cp*RhCl₂]₂-catalyzed formal [3 + 2] cycloaddition involving a sequential coupling reaction initiated by C–H activation and aza-Michael addition has been developed for the general and efficient synthesis of 1,2-dihydropyrrolo[3,4-b]indol-3-ones.

Funder

Natural Science Foundation of Tianjin City

National Natural Science Foundation of China

Tianjin Normal University

Tianjin University

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/QO/D0QO00922A

Reference67 articles.

1. Leucomidines A–C, novel alkaloids from Leuconotis griffithii

2. Phosphoric Acid Catalyzed Desymmetrization of Bicyclic Bislactones Bearing an All-Carbon Stereogenic Center: Total Syntheses of (−)-Rhazinilam and (−)-Leucomidine B

3. Enantioselective Total Syntheses of (−)-Rhazinilam, (−)-Leucomidine B, and (+)-Leuconodine F

4. Synthesis of rigid, heterocyclic dipeptide analogs

5. From pyrroles to 1-oxo-2,3,4,9-tetrahydro-1H-β-carbolines: A new class of orally bioavailable mGluR1 antagonists