6808-65-7

Basic information

• Product Name: 2-(1,3-benzodioxol-5-yl)quinoline
• Synonyms: C10661;Dubamine;Quinoline, 2-(1,3-benzodioxol-5-yl)-
• CAS NO: 6808-65-7
• Molecular Formula: C₁₆H₁₁NO₂
• Molecular Weight: 249.264
• Mol File: 6808-65-7.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 424.2°C at 760 mmHg
• Flash Point: 153.1°C
• Density: 1.289g/cm³
• Vapor Pressure: 5.2E-07mmHg at 25°C
• Refractive Index: 1.678
• CAS DataBase Reference: 2-(1,3-benzodioxol-5-yl)quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1,3-benzodioxol-5-yl)quinoline(6808-65-7)
• EPA Substance Registry System: 2-(1,3-benzodioxol-5-yl)quinoline(6808-65-7)

Safety Data

• Hazardous Substances Data: 6808-65-7(Hazardous Substances Data)

Usage

Chemical composition

Consists of a quinoline core with a 1,3-benzodioxole substituent at the 2-position.

Type of compound

Heterocyclic compound.

Potential activities

Has potential pharmacological and biological activities.

Applications

Has been studied for potential use in medicinal chemistry and drug development.

Possible uses

May be used in the treatment of various diseases and conditions.

Significance

Is an interesting target for further research and potential exploitation in the pharmaceutical industry.

Upstream product

• 5208-87-7 1'-hydroxysafrole 
• 615-43-0 2-iodophenylamine 
• 57134-53-9 3,4-methylenedioxyphenylethyne 
• 271-58-9 anthranil 
• 2005-43-8 2-bromoquinoline 
• 94839-07-3 3,4-(methylenedioxy)-benzeneboronic acid 
• 552-89-6 2-nitro-benzaldehyde 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 1252015-01-2 (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(2-nitrophenyl)prop-2-en-1-one 
• 103-63-9 1-phenyl-2-bromoethane 
• 4421-09-4 piperonylonitrile 
• 5344-90-1 2-Aminobenzyl alcohol 
• 5876-51-7 5-iodo-1,3-benzodioxole 
• 6329-73-3 1-benzo[1,3]dioxol-5-yl-ethanol 

Downstream Products

• 4179-37-7 graveolinine 
• 485-61-0 graveoline 

Relevant articles and documents

A Domino Heck Coupling-Cyclization-Dehydrogenative Strategy for the One-Pot Synthesis of Quinolines

An efficient, one-pot, domino synthesis of quinolines via the coupling of iodoanilines with allylic alcohols facilitated by palladium catalysis is described. The overall synthetic process involves an intermolecular Heck coupling between 2-iodoanilines and allylic alcohols, intramolecular condensation of in situ generated ketones with an internal amine functional group, and a dehydrogenation sequence. Notably, this protocol occurs in water as a green solvent. Significantly, the method exhibits broad substrate scope and is applied for the synthesis of deuterated quinolines through a deuterium-exchange process.

NiH-Catalyzed Hydroamination/Cyclization Cascade: Rapid Access to Quinolines

Despite the significant success of metal-H-catalyzed hydroamination methodologies, considerable limitations still exist in the selective hydroamination of alkynes, especially for terminal alkynes. Herein, we develop a highly efficient NiH catalytic system that activates readily available alkynes for a cascade hydroamination/cyclization reaction with anthranils. This mild, operationally simple protocol is amenable to a wide array of alkynes including terminal and internal, aryl and alkyl, electron-deficient and electron-rich ones, delivering structurally diverse quinolines in useful to excellent yields (>80 examples, up to 93% yield). The utility of this procedure is exhibited in the late-stage functionalization of several natural products and in the concise synthesis of an antitumor molecule graveolinine and a triplex DNA intercalator. Preliminary mechanistic experiments suggest an alkenylnickel-mediated alkyne hydroamination and an intramolecular cyclization/aromatization of putative enamine intermediates.

Asymmetric Synthesis of Hydroquinolines with α,α-Disubstitution through Organocatalyzed Kinetic Resolution

The first kinetic resolution of hydroquinoline derivatives with α,α-disubstitution has been achieved through asymmetric remote aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. Mechanistic studies suggest a monomeric catalyst pathway proceeding through rate- and enantio-determining electrophilic attack promoted by a network of attractive non-covalent interactions between the substrate and catalyst. Facile subsequent removal and transformations of the newly introduced hydrazine moiety enable these protocols to serve as powerful tools for asymmetric synthesis of N-heterocycles with α,α-disubstitution.