Regiodivergent Synthesis of 11<i>H</i>‐Indolo[3,2‐<i>c</i>]quinolines and Neocryptolepine from a Common Starting Material-Reference-Cited by-同舟云学术

Regiodivergent Synthesis of 11H‐Indolo[3,2‐c]quinolines and Neocryptolepine from a Common Starting Material

Published:2023-03-09 Issue:13 Volume:26 Page:
ISSN:1434-193X
Container-title:European Journal of Organic Chemistry
language:en
Short-container-title:Eur J Org Chem

Author:

Håheim Katja S.¹,Lund Bjarte Aarmo²,Sydnes Magne O.¹^ORCID

Affiliation:

1. Department of Chemistry, Bioscience and Environmental Engineering University of Stavanger NO-4036 Stavanger Norway

2. Department of Chemistry UiT The Arctic University of Norway NO-9037 Tromsø Norway

Abstract

AbstractA large number of diversely functionalized analogs of the bioactive natural products neocryptolepine and isocryptolepine have been prepared from a series of 3‐bromoquinoline derivatives. The neocryptolepines were obtained by a Pd0‐catalyzed C−C bond coupling followed by C−N bond formation in yields up to 80 %, whereas the indoloquinolines were prepared by a Suzuki‐Miyaura cross‐coupling followed by azidation‐photochemical cyclization in yields ranging from traces to 95 % yield.

Funder

Universitetet i Stavanger

Norges Forskningsråd

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejoc.202300137

Reference46 articles.

1. For some recent papers describing the synthesis of isocryptolepine and neocryptolepine see for example:

2. A Compilation of Synthetic Strategies to Access the Most Utilized Indoloquinoline Motifs