1-Acryloyl-2-cyanoindole: A Skeleton for Visible-Light-Induced Cascade Annulation

Abstract

1-Acryloyl-2-cyanoindoles were found to be novel and efficient skeletons in visible-light-induced persulfate-promoted cascade cyclization reactions. With this transition-metal-free photocatalytic procedure, various sulfonated/thiocyanated pyrrolo[1,2a]indolediones were synthesized from 1-acryloyl-2-cyanoindoles with sulfonyl hydrazides/NH 4 SCN at room temperature under mild reaction conditions.

Visible-Light-Promoted Phosphorylation/Cyclization of 1-Acryloyl-2-cyanoindoles in Green Solvent

“…High-resolution mass spectroscopy (HRMS) was taken with a 3000-mass spectrometer, using a Waters Q-Tof MS/MS system with the ESI technique. Starting materials 1a – 1m were synthesized according to the literature . Starting materials 2 were purchased from Shanghai Bide Pharmatech Co. Ltd.…”

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

“…Yu's group achieved the synthesis of sulfonated/ thiocyanated [111] and phosphorylated [112] pyrrolo[1,2a]indolediones by reacting of 1-acryloyl-2-cyanoindoles with sulfonyl hydrazides, NH 4 SCN or phosphine oxides under visiblelight-induced and persulfate-promoted conditions (Scheme 67). Mechanistically, the addition of radical 67-A to the C=C bond of alkene followed by intramolecular cyclization provides iminyl radical 67-C.…”

Electrochemical Oxidation Involving Sulfonyl Hydrazine for the Synthesis of 2‐Sulfonyl Quinolines/Pyridines

“…[12,13] For example, sulfonyl hydrazides are commonly used reagents in organic synthesis due to their interesting properties and reactivity. [14,15] Sulfonyl hydrazides are easily obtained by the reaction of the corresponding sulfonyl chlorides [16] with aqueous hydrazine solutions, are inexpensive and easy to handle experimentally, and they generally exist in stable solid forms that are relatively less sensitive to air than other sulfur-containing reagents. Therefore, in the past two decades, based on its many advantages in the field of chemistry, [17] chemists have widely used sulfonyl hydrazides to synthesize some organic molecules.…”

“…Moreover, sulfonyl group is a wide range of synthetic groups [12,13] . For example, sulfonyl hydrazides are commonly used reagents in organic synthesis due to their interesting properties and reactivity [14,15] . Sulfonyl hydrazides are easily obtained by the reaction of the corresponding sulfonyl chlorides [16] with aqueous hydrazine solutions, are inexpensive and easy to handle experimentally, and they generally exist in stable solid forms that are relatively less sensitive to air than other sulfur‐containing reagents.…”