3352-05-4

Basic information

• Product Name: 1-Indolizinecarbonitrile
• Synonyms: 1-Cyanoindolizin;1-Indolizinecarbonitrile;1-cyano-indolizine;1-Cyan-indolizin
• CAS NO: 3352-05-4
• Molecular Formula: C9H6N2
• Molecular Weight: 142.16
• Mol File: 3352-05-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1-Indolizinecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Indolizinecarbonitrile(3352-05-4)
• EPA Substance Registry System: 1-Indolizinecarbonitrile(3352-05-4)

Safety Data

• Hazardous Substances Data: 3352-05-4(Hazardous Substances Data)

Usage

General Description

1-Indolizinecarbonitrile, also known as indolizine-1-carbonitrile, is a chemical compound with the molecular formula C9H6N2. It is a heterocyclic compound that contains both nitrogen and carbon atoms in its structure. 1-Indolizinecarbonitrile has been used as a starting material in the synthesis of various pharmaceutical and agrochemical products. The compound is also known for its potential biological activities and is of interest in medicinal chemistry research. It is used as a building block in the synthesis of various organic compounds and has potential applications in the development of new drug molecules. Additionally, 1-Indolizinecarbonitrile has been investigated for its potential environmental and industrial applications due to its unique chemical properties and reactivity.

Upstream product

• 6266-23-5 1-(carboxymethyl)pyridinium chloride 
• 109-75-1 but-3-enenitrile 
• 107-20-0 2-chloroethanal 
• 2739-97-1 pyridine-2-acetonitrile 
• 110-86-1 pyridine 
• 394212-91-0 methyl 1-cyanoindolizine-3-carboxylate 
• 188816-65-1 3-amino-1-cyano-4H-pyrido<1,2-a>pyridin-4-one 
• 394212-97-6 1-cyanoindolizine-3-carboxylic acid 
• 107-13-1 acrylonitrile 
• 920-34-3 2-bromoacrylonitrile 
• 111198-06-2 1-[(benzotriazol-1-yl)methyl]pyridinium chloride 

Downstream Products

• 1246845-71-5 methyl 4-(1-cyanoindolizine-3-yl) benzoate 
• 1246844-51-8 4-(1-Cyanoindolizine-3-yl)-2-hydroxybenzoic acid 
• 1246844-35-8 4-(1-cyanoindolizine-3-yl)benzoica acid 
• 1246845-72-6 methyl 4-(1-cyanoindolizine-3-yl)-2-methoxymethoxybenzoate 
• 1403889-41-7 3,3'-((4-methoxyphenyl)methylene)diindolizine-1-carbonitrile 
• 1403889-43-9 3,3'-((4-chlorophenyl)methylene)diindolizine-1-carbonitrile 
• 1403889-42-8 3,3'-(phenylmethylene)diindolizine-1-carbonitrile 
• 1394827-43-0 3-(2-bromophenyl)indolizine-1-carbonitrile 
• 1394827-41-8 3-o-tolylindolizine-1-carbonitrile 
• 1394827-37-2 3-(3-formylphenyl)indolizine-1-carbonitrile 
• 1394827-39-4 3-(3-(trifluoromethyl)phenyl)indolizine-1-carbonitrile 
• 1394827-32-7 3-(3-chlorophenyl)indolizine-1-carbonitrile 
• 1394827-36-1 3-(3-fluorophenyl)indolizine-1-carbonitrile 
• 1394827-30-5 3-m-tolylindolizine-1-carbonitrile 

Relevant articles and documents

Visible-Light-Induced Regioselective Dicarbonylation of Indolizines with Oxoaldehydes via Direct C-H Functionalization

A metal-free system for regioselective dehydrogenative cross-couplings between indolizines and oxoaldehydes catalyzed by visible light under mild conditions has been described. As an atom economical and eco-friendly protocol, the reaction proceeds in good yields using inexpensive, readily available visible-light sources and the environmentally friendly oxidant oxygen. Various valuable 1,2-dicarbonyl derivatives attached to an indolizine core were easily accessed by the direct dicarbonylation of the sp2 C-H bond.

Synthesis of indolizine derivatives with selective antibacterial activity against Mycobacterium tuberculosis

1-Substituted indolizines with activity against Mycobacterium tuberculosis have been synthesized. The most active compounds carry an hydroxyphenylmethyl- or hydroxyalkyl substituent in the indolizine 1-position. The alkyl chain should be moderately long (C-5 or C-6). Aryl groups in the 2- and 3-position of the indolizine are also required. Removal of the 3-substituent resulted in significant loss of activity. A nitrile substituent in the 7-position is beneficial for both chemical stability and bioactivity. The compounds studied display a narrow antibacterial spectrum and appear to be quite selective antimycobacterial compounds. Moderate activity against certain pathogenic protozoa was also observed.

Ring contractions of 4-oxoquinolizine-3-diazonium tetrafluoroborates, by an aza wolff rearrangement, to alkyl indolizine-3-carboxylates

The 1-substituted 3-amino-4H-quinolizin-4-ones 13, available in two steps from 10 and methyl (Z)-2-benzyloxycarbonylamino-3-(dimethylamino)propenoate (11), were diazotized to give the stable diazonium tetrafluoroborates 7a and 7b. Heating of these diazonium salts in alcohols gave mixtures of 3-unsubstituted quinolizine derivatives 8a and 8b and the alkyl indolizine-3-carboxylates 9a-h. The ratio of the two types of products 8 and 9 was dependent on the type of alcohol employed. Thus, treatment of 7a or 7b with 2-propanol predominantly resulted in the 3-unsubstituted quinolizinones 8, while treatment of 7a or 7b with primary alcohols gave the indolizine-3-carboxylates 9 as the major products in most cases. The transformation of the 4-oxoquinolizine-3-diazonium tetrafluoroborates 7a and 7b into the alkyl indolizine-3-carboxylates 9a-h represents the first example of a Wolff rearrangement in the fused cyclic α-diazoamide series.