3352-06-5

Usage

Type of compound

heterocyclic aromatic compound

Structure

consists of an indolizine ring system and a carbonitrile functional group

Attachment position

carbonitrile group attached to the 3-phenyl position

Usage

building block in organic synthesis

Interest

potential biological activities in pharmaceutical and medicinal chemistry

Application

development of advanced materials

Utility

versatile and specific reagent in academic research

Upstream product

• 110-86-1 pyridine 
• 920-37-6 2-Chloroacrylonitrile 
• 4460-46-2 3-chloro-3-phenyl-3H-diazirine 
• 115732-59-7 phenylchloropyridinium ylide 
• 1126444-26-5 C₉H₅ClN₂ 
• 98-80-6 phenylboronic acid 
• 2739-97-1 pyridine-2-acetonitrile 
• 536-74-3 phenylacetylene 
• 140-10-3 (E)-3-phenylacrylic acid 
• 100-39-0 benzyl bromide 
• 2589-31-3 N-benzylpyridinium bromide 
• 107-13-1 acrylonitrile 
• 3352-05-4 indolizine-1-carbonitrile 
• 80-17-1 benzenesufonyl hydrazide 

Relevant academic research and scientific papers

An I2-catalyzed oxidative cyclization for the synthesis of indolizines from aromatic/aliphatic olefins and α-picoline derivatives

A novel I2-catalyzed intermolecular oxidative tandem cyclization reaction of aromatic/aliphatic olefins and α-picoline derivatives has been achieved for the synthesis of indolizines under metal-free conditions. In this transformation, substituted indolizines are obtained in moderate to good yields through C-C/C-N bond formation in one pot. This journal is

Application of primary halogenated hydrocarbons for the synthesis of 3-Aryl and 3-Alkyl indolizines

Indolizine is an important heterocyclic compound with several interesting properties that make it suitable for numerous applications in many fields, such as biology, medicine and materials. However, the synthesis of 3-Alkyl indolizines from bulky primary halogenated alkanes has not yet been reported. Herein, a transition-metal-free synthetic route to 3-Aryl and 3-Alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons has been reported for the first time using a tandem reaction. The key step of this method is the oxidative dehydrogenative aromatization of a tetrahydroindolizine intermediate with 2,2,6,6-Tetramethylpiperidine-N-oxyl (TEMPO) as the oxidant. The advantages of this protocol are its use of easily available and low-cost starting materials, the transition-metal-free conditions and its ready scalability.

Synthesis of substituted indolizines via radical oxidative decarboxylative annulation of 2-(pyridin-2-yl)acetate derivatives with α,β-unsaturated carboxylic acids

A copper mediated radical oxidative annulation of 2-(pyridin-2-yl)acetate derivatives with α,β-unsaturated carboxylic acids is developed. This study offers a new and expedient strategy for the synthesis of useful indolizines in moderate to good yields and exhibits a broad substrate scope and good functional group tolerance.

Palladium-catalyzed C-3 desulfitative arylation of indolizines with sodium arylsulfinates and arylsulfonyl hydrazides

Derivatized indolizines were efficiently prepared by direct C-3 arylation of indolizines using sodium arylsulfinates and arylsulfonyl hydrazides. Pd-catalyzed desulfitative C-3 arylation with sodium arylsulfinates was achieved with the assistance of peroxides, and the catalytic efficiency was promoted by N-containing ligands. Arylsulfonyl hydrazides were also successfully applied in Pd-catalyzed desulfitative C-3 arylation with indolizines, and the side homocoupling reactions can be restrained in the component solvent under milder conditions. Various derivatives were synthesized in good yields by both methods, offering expedient protocols for the synthesis of C-3 functionalized indolizine molecules.

Desulfitative palladium-catalyzed direct C-3 arylation of indolizines with arylsulfonyl chlorides

An efficient Pd-catalyzed desulfitative approach to C-3 arylation of indolizine derivatives has been developed, and the protocol uses readily available arylsulfonyl chlorides as the arylation reagent under nitrogen. This transformation was performed in a mixed solvent of 1-methyl-2-pyrrolidone and dimethoxyethane using simple triphenylphosphine as a ligand, which provides a new method for the C-3 arylation of indolizines. An efficient Pd-catalyzed desulfitative approach to C-3 arylation of indolizine derivatives has been developed, the protocol using readily available arylsulfonyl chlorides as the arylation reagent under nitrogen. This transformation proceeds in a mixed solvent of NMP and DME using simple triphenylphosphine a ligand, and provides a new method for the C-3 arylation of indolizines.

Indolizine Synthesis via Oxidative Cross-Coupling/Cyclization of Alkenes and 2-(Pyridin-2-yl)acetate Derivatives

A novel copper/I2-mediated oxidative cross-coupling/cyclization of 2-(pyridin-2-yl)acetate derivatives and simple olefins is developed, which provides a straightforward and efficient access to structural diversely indolizines. A series of 1,3-d

Tuning radical reactivity using iodine in oxidative C(sp3)-H/C(sp)-H cross-coupling: An easy way toward the synthesis of furans and indolizines

Molecular iodine was found to be an effective redox catalyst for the oxidative cross-coupling of carbonyl compounds with terminal alkynes. In this work, we demonstrated that iodine could tune radical reactivity through reversible C-I bond formation for co

Palladium catalyzed oxidative Suzuki coupling reaction of indolizine at the 3-position using oxygen gas as the only oxidant

Stoichiometric metal oxidant applied in the functionalization of indolizine at the 3-position through C-H activation in a previous report was found to increase the cost of the synthesis and worsen the environmental pollution. In this paper, we developed a Pd(OAc)2/O2 catalytic system with or without ligands for an oxidative Suzuki coupling reaction of indolizine at the 3-position through C-H activation. As reported in the literature, some indolizines dimerized when catalyzed by palladium acetate under ligand-free conditions. However, we found that the dimerization of 2,3-unsubstituted indolizines was inhibited by the addition of ligands. Based on this finding, the arylation of these indolizines can be successfully achieved via a Pd(OAc)/O2 system using picolinic acid as a ligand. 1,2-disubstituted indolizines that do not easily dimerize can react smoothly with arylboronic acids under ligand-free conditions. Furthermore, broad group tolerance was shown in both indolizine and arylboronic acid. Finally, this method has the advantages of mild conditions, a broad array of starting materials and the use of a green oxidant. The Royal Society of Chemistry 2014.

Silver-mediated synthesis of indolizines via oxidative C-H functionalization and 5-endo-dig cyclization

An efficient strategy for the synthesis of indolizines from readily available starting materials via oxidative C-H functionalization and 5-endo-dig cyclization in one step has been demonstrated. This protocol represents wide substrate scope, high function

Pd-Catalyzed C-3 functionalization of indolizines via C-H bond cleavage

New transition metal-catalyzed methods for the arylation of indolizines by the direct cleavage of C-H bonds have been developed. A wide range of aryltrifluoroborate salts react with indolizines in the presence of Pd(OAc) 2 catalyst and AgOAc oxidant to give the arylated indolizines in high yields. Both electron-donating and electron-withdrawing groups perform smoothly while bromide and chlorine substituents are tolerated. In addition, the indolizines display similar reactivities in the Pd-catalyzed reaction with 3-phenylpropiolic acid to afford the corresponding C-3 alkynylated indolizines. These methods allow the direct functionalization of indolizines in one step.