124957-63-7

Usage

Classification

Azido compound

Use

Building block in organic synthesis, preparation of various organic compounds, potential applications in photochemistry and materials science

Hazards

Potential hazards associated with azide functional group

Unique properties

Unique structure and reactivity in the field of organic chemistry

Upstream product

• 124957-36-4 Methyl 3-acetoxy-2-methylene-3-phenylpropanoate 
• 18020-59-2 methyl 3-hydroxy-2-methylidene-3-phenylpropionate 
• 100-52-7 benzaldehyde 
• 103669-71-2 (Z)-methyl 2-(bromomethyl)-3-phenylacrylate 

Downstream Products

• 889855-43-0 methyl (E)-2-[(tert-butoxycarbonylamino)methyl]-3-phenylacrylate 

Relevant academic research and scientific papers

Fast and efficient preparation of Baylis-Hillman-derived (E)-allylic azides and related compounds in aqueous medium

A practical access to alkyl- and aryl-substituted (E)-2-(azidomethyl)alkenoates and related azido compounds from the corresponding allylic bromides in aqueous acetone is described. An alternative method to obtain the starting bromides based on heterogeneo

Synthesis and cytotoxicity of Baylis-Hillman template derived betulinic acid-triazole conjugates

Several alkynes and azides were prepared starting from betulinic acid and Baylis-Hillman reaction-derived allylic alcohols. These alkynes and azides were then coupled under click cycloaddition conditions to obtain functionalized betulinic acid-triazole conjugates. Similarly, pyrazinyl- and indolylbetulinic acid-triazoles were also prepared employing cycloaddition chemistry. All the synthetic compounds were tested for their cytotoxicity against murine breast cancer (4T1) and human pancreatic cancer (MIA PaCa-2) cell lines. Based on these in vitro assays, two series of compounds have been identified as lead compounds for further development.

2-Azetidinones: Synthesis and biological evaluation as potential anti-breast cancer agents

A series of twenty-five 2-azitidinone (β-lactam) derivatives were synthesized and evaluated for anti-cancer properties against breast cancer, MCF-7 and MDA-MB-231. These β-lactam derivatives depicted significant cytotoxicity in cancer cell lines but not i

Copper-catalyzed direct transformation of secondary allylic and benzylic alcohols into azides and amides: An efficient utility of azide as a nitrogen source

A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has been successfully adapted to the preparation of azides directly from their corresponding alcohols and offers excellent chemoselectivity in the formation of ω-halo azides and the azidation of allylic alcohols in the presence of a benzyl alcohol moiety. In addition, this strategy provides an opportunity to synthesize azides that can serve as precursors to β-amino acids. A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has also been adapted to the preparation of azides directly from their corresponding alcohols.

N-bromosuccinimide-mediated radical cyclization of 3-arylallyl azides: Synthesis of 3-substituted quinolines

Visible light irradiation of N-bromosuccinimide serves as an effective means to convert methyl 2-(azidomethyl)-3-arylpropenoates and 2-(azidomethyl)-3-arylacrylonitriles to the corresponding iminyl radicals via ?±-hydrogen abstraction and subsequent extrusion of dinitrogen. Thus formed iminyl radicals then undergo intramolecular ortho attack on the aryl ring, affording methyl quin-oline-3-carboxylates and quinoline-3-carbonitriles respectively.

Synthesis of chiral β2-amino acids by asymmetric hydrogenation

The synthesis of chiral β2-amino acids by homogeneous asymmetric hydrogenation is discussed. Prochiral β-aryl- or β-hetaryl-α-N-benzyl/N-acetyl/N-Boc substituted α- aminomethylacrylates used as substrates were prepared by a Baylis-Hillman react

Utility of allylic azides for the synthesis of fused triazoles and tetrazoles via intramolecular cycloaddition

The synthesis of a variety of annulated triazoles and tetrazoles from differently substituted allyl azides, afforded from the Baylis-Hillman adduct of acrylates, using intramolecular cycloaddition approach is described. Georg Thieme Verlag Stuttgart.

Solvent free synthesis of 1,5-disubstituted tetrazoles derived from Baylis Hillman acetates as potential TNF-α inhibitors

Solvent free multicomponent reaction of Baylis Hillman acetate, TMS azide and arylnitrile to produce 1,5-disubstituted tetrazole is described. Some of these tetrazoles are found to be potential TNF-α inhibitors.

SEVEN-MEMBERED RING COMPOUND, PRODUCTION METHOD THEREOF AND PHARMACEUTICAL USE THEREOF

A 7-membered heterocyclic compound having the formula (I), or its salt, or a solvate thereof with a chymase inhibitory action and useful for the prevention or treatment of various diseases, in which chymase is involved: a method for producing the same, and a pharmaceutical composition useful for the prevention or treatment of diseases, in which chymase is involved, including the compound of having the formula (I), or its pharmaceutically acceptable salt, or a solvate thereof are provided.

7-MEMBERED RING COMPOUND, PROCESS FOR PRODUCING THE SAME, AND MEDICINAL USE THEREOF

A 7-membered heterocyclic compound having the formula (I), or its salt, or a solvate thereof with a chymase inhibitory action and useful for the prevention or treatment of various diseases, in which chymase is involved: a method for producing the same, and a pharmaceutical composition useful for the prevention or treatment of diseases, in which chymase is involved, including the compound of having the formula (I), or its pharmaceutically acceptable salt, or a solvate thereof are provided.