Organocatalytic formal [3 + 3] cyclization of α-(6-indolyl) propargylic alcohols.

Org Biomol Chem

Department of Medicinal Chemistry, School of Pharmacy, Qingdao University, Qingdao 266021, China.

Published: August 2022

With the aid of acetic acid, a 1,10-conjugate addition-mediated formal [3 + 3] cyclization of alkynyl indole imine methides formed from α-(6-indolyl) propargylic alcohols with 1,3-dicarbonyl compounds such as 4-hydroxycoumarins and cyclohexane-1,3-diones was developed, which provided robust access to a wide range of pyranocoumarin and pyran derivatives containing an indole skeleton with high efficiency under mild conditions.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d2ob01206eDOI Listing

Publication Analysis

Top Keywords

formal cyclization
8
α-6-indolyl propargylic
8
propargylic alcohols
8
organocatalytic formal
4
cyclization α-6-indolyl
4
alcohols aid
4
aid acetic
4
acetic acid
4
acid 110-conjugate
4
110-conjugate addition-mediated
4

Similar Publications

An unprecedented formal [1+5] cyclization of indoline-derived azadienes with 1,3,5-triazinanes has been realized, providing a facile access to biologically important indoline-spiro-hexahydropyrimidines with good to excellent yields (up to 99% yield). Different from previous reports, this is the first study that indoline-derived azadienes could participate in cyclizations as one-atom synthons. This methodology is also distinguished by not involving any additive or catalyst, readily available starting materials, wide range of substrate applicability, operational simplicity and simultaneously reassembling two C-N and two C-C bonds in one-step reaction.

View Article and Find Full Text PDF

In this work, a switchable synthesis of β-ketosulfone and α-chloroketone through a radical difunctionalization of alkenes is reported. The transformation works well under iron peroxo species/photoredox dual catalysis and an open-flask atmosphere, and the reaction is highlighted with good yields and a broad reaction scope. Mechanism studies show that the reaction is initiated by a formal [4 + 2] cyclization of the sulfonyl radical in a regioselective manner.

View Article and Find Full Text PDF

Photoredox/Iron Dual-Catalysis-Enabled [4 + 2] Cyclization of Acyl Nitrene with Alkynes.

Org Lett

December 2024

College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, China.

In this work, the annulation of acyl nitrene with alkynes is reported under photoredox/iron dual-catalysis for the synthesis of a series of isoquninalin-2-ones. The reaction is featured with a high reaction regioselectivity and good reaction generality. In particular, the resulting isoquinalin-2-ones could be structurally elaborated into several biologically interesting scaffolds.

View Article and Find Full Text PDF

We herein report the serendipitous discovery of the interrupted Plancher rearrangement initiated by an HFIP-promoted dearomative epoxide-indole cyclization, unlocking a new blueprint to the formal C3 umpolung reactivity of indoles. This rapid complexity generating cascade process paves the way toward a new class of fused-bridged indolines in high yields and under full regio- and diastereocontrol. The reaction is amenable to a wide range of substituents in the starting materials.

View Article and Find Full Text PDF

Pyridazine derivatives hold significant interest due to their broad applications in pharmaceuticals and materials science, where they serve as valuable scaffolds for bioactive compounds and functional materials. Here, we report a formal [4 + 2] reaction for the synthesis of 5'-sulfonyl-4'-aryl-3-cyano substituted pyridazine compounds from the reaction between vinylogous enaminonitriles and sulfonyl hydrazides. The key features of our pyridazine synthesis include the transamidation of vinylogous enaminonitriles with sulfonyl hydrazide, radical sulfonylation of the resulting intermediate, and subsequent 6-endo-trig radical cyclization.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!