36343-07-4

Upstream product

• 102-92-1 cinnamoyl chloride 
• 2450-71-7 Propargylamine 

Downstream Products

• 1227164-63-7 C₁₄H₁₃NO₃ 
• 1220393-62-3 5-methyl-2-styryloxazole 
• 1214922-14-1 (E)-5-(iodomethylene)-2-((E)-styryl)-4,5-dihydrooxazole 
• 1214921-90-0 (E)-5-methylene-2-styryl-4,5-dihydrooxazole 
• 1309977-63-6 (E)-5-(bromomethylene)-2-styryl-4,5-dihydrooxazole 
• 1309977-61-4 (E)-5-(dibromomethylene)-2-styryl-4,5-dihydrooxazole 
• 1309977-53-4 N-{5-bromo-2-[(E)-2-phenylvinyl]-4H-1,3-oxazin-6-yl}-N,4-dimethylbenzenesulfonamide 
• 1309977-48-7 N-{5-chloro-2-[(E)-2-phenylvinyl]-4H-1,3-oxazin-6-yl}-N,4-dimethylbenzenesulfonamide 
• 1220393-61-2 C₁₅H₁₅NO 

Relevant academic research and scientific papers

Base-Promoted Cycloisomerization for the Synthesis of Oxazoles and Imidazoles

Treatment of propargylamides or propargylamidines with cesium carbonate in DMSO results in the formation of the corresponding oxazoles or imidazoles in good yields. A large variety of substrates with various functional groups are tolerated. DFT study on a model substrate reveals that the reactions proceed via a sequence involving allene formation, intramolecular cyclization, and double-bond isomerization.

AMINE-BORANES AS BIFUNCTIONAL REAGENTS FOR DIRECT AMIDATION OF CARBOXYLIC ACIDS

The present invention generally relates to a process for selective and direct activation and subsequent amidation of aliphatic and aromatic carboxylic acids to afford an amide R3CONR1R2. That the process is capable of delivering gaseous or low-boiling point amines provides a major advantage over existing methodologies, which involves an intermediate of triacyloxyborane-amine complex [(R3CO2)3—B—NHR1R2]. This procedure readily produces primary, secondary, and tertiary amides, and is compatible with the chirality of the acid and amine involved. The preparation of known pharmaceutical molecules and intermediates has also been demonstrated.

Fluorocyclization of Allyl Alcohols and Amines to Access 3-Functionalized Oxetanes and Azetidines

An efficient method to prepare 3-functionalized oxetanes and azetidines has been realized by fluorocyclization of readily available 2-azidoallyl/2-alkoxyallyl alcohols and amines. Notably, this is the first example applying the fluorocyclization strategy to construct four-membered heterocycles. The pendant electron-donating group (-N3 or -OR) plays a crucial role in polarizing the C= C double bond and facilitating the cyclization process, as verified by DFT and experimental studies.

Zn(OTf)2-catalyzed, microwave-promoted synthesis of 2-substituted 5-methyloxazoles from propargylic amides

The versatile conversion of propargylic amides to the respective 2-substituted 5-methyloxazoles was efficiently catalyzed by Zn(OTf)2 (5 mol%) under microwave irradiation in toluene. The method was applicable to a wide range of aliphatic, aroma

Silver-Catalyzed Cyclization of Propargylic Amides to Oxazolines

A ligand-accelerated effect is observed in the cyclization of propargylic amides catalyzed by bis(pyridyl)silver(I) complexes, with an unexpected reversal of electronic demand to the analogous NH addition reaction. The catalyst was found to be effective for internal alkyne substrates, offering exclusive selectivity for the 5-exo-dig product. Differences in selectivity profile between gold- and silver-catalyzed processes are highlighted and discussed.

2-Oxazol-5-ylethanones by consecutive three-component amidation-coupling- cycloisomerization (ACCI) sequence

Substituted oxazol-5-ylethanones can be synthesized in a consecutive three-component sequence starting from propargylamine and various acid chlorides, both for amidation and cross-coupling. Therefore, this diversity-oriented one-pot approach to substitute