112602-04-7Relevant academic research and scientific papers
STEREOSELECTIVE SYNTHESES OF SPICY COMPONENTS IN PEPPERS
Ohta, Akihiro,Tonomura, Yoshiko,Sawaki, Junko,Naohito, Sato,Akiike, Hitomi,et al.
, p. 965 - 973 (1991)
The syntheses of (E)-α,β-unsaturated amides were accomplished from chloroacetamides and alkyl halides via β-elimination of the pyrazinyl-sulfinyl group, and some of the products are spicy components of piperaceous plants.
First mechanosynthesis of piperlotines A, C, and derivatives through solvent-free Horner–Wadsworth–Emmons reaction
Ramírez-Marroquín, Oscar Abelardo,Manzano-Pérez, Flavio,López-Torres, Adolfo,Hernández-López, Alejandro,Cortés-Pacheco, Abimelek,Reyes-González, Miguel Angel
, p. 244 - 255 (2019/01/22)
Piperlotines are natural products characterized by an α,β-unsaturated amide moiety. These compounds found wide applications in Medicinal Chemistry like antibacterials, cytotoxic agents, anticoagulants, among others. To date, diverse methods of synthesis have been reported for piperlotines, but involving the use of catalysts, hazard reagents, anhydrous media or coupling reagents. Thus, in this work, we developed a greener method of synthesis of piperlotines A, C, and derivatives, through mechanochemical activation under solvent-free conditions. The reaction of a β-amidophosphonate, K2CO3, and an aromatic aldehyde afforded target compounds in moderate to good yields (46–77%), in an open atmosphere by grinding. It is worth to mention that this mechanochemical process was under thermodynamic control because just E isomer was isolated for every reaction. Moreover, synthesized piperlotines have been predicted by means of chemoinformatic analysis as potential therapeutic agents for the treatment of arthritis or cancer.
A FACILE AND HIGHLY STEREOSELECTIVE SYNTHESIS OF (2E)-, (2E,4E)-UNSATURATED AMIDES AND RELATED NATURAL PRODUCTS
Huang, Y. Z.,Shi, Lilan,Yang, Jianhua,Zhang, Jingtao
, p. 2159 - 2162 (2007/10/02)
A facile synthesis of (2E)- and (2E, 4E)-unsaturated amides was achieved via arsonium bromides with high stereoselectivity.Its application to the synthesis of related natural products 4 and 5 is also reported.
