95465-44-4Relevant articles and documents
Regio- and diastereoselective ene reaction of 4-phenyl-1,2,4- triazoline-3,5-dione with chiral allylic alcohols and their derivatives
Gau, Ay-Hua,Lin, Guey-Liang,Uang, Biing-Jiun,Liao, Fen-Ling,Wang, Sue-Lein
, p. 2194 - 2201 (1999)
Chiral allylic alcohols 1a-e reacted with 4-phenyl-1,2,4-triazoline- 3,5-dione (PTAD) in CH2Cl2 to produce 3-amino-1-alken-4-ols 2 and 3 in 78- 89% yields, with 68-90% diastereomeric excess (de) in favor of the threo isomer. Chiral allylic ethers 1f,g and acetates 1h,i gave similar yields but lower de (34-66%). Reaction of allylic alcohols 6a-e with PTAD in CH2Cl2 produced 1,3-regioisomers 7 and 8 exclusively in 33-65% yields without apparent diastereoselectivity, except when R1 was a Bu(t) group, in which case only syn product 7 was formed. However, when 6a or 6c was subjected to reaction with PTAD in a polar solvent, up to 88% de was observed. Reaction of allylic ethers 6f,g and acetates 6h,i with PTAD in CH2Cl2 also produced 7 and 8 exclusively with improved yields (56-96%) and diastereoselectivity (50- 100% de in favor of the syn isomer).
Visible Light Mediated Photocatalytic N-Radical Cascade Reactivity of O,δ-Unsaturated N-Arylsulfonylhydrazones: A General Approach to Structurally Diverse Tetrahydropyridazines
Azzi, Emanuele,Ghigo, Giovanni,Parisotto, Stefano,Pellegrino, Francesco,Priola, Emanuele,Renzi, Polyssena,Deagostino, Annamaria
, p. 3300 - 3323 (2021/02/16)
Tetrahydropyridazines are of particular interest for their versatility as intermediates in organic synthesis and display pharmacological activity in several domains. Here, we describe the photocatalytic synthesis of different tetrahydropyridazines starting from O,δ-unsaturated N-arylsulfonylhydrazones. Simple structural changes of substrates result into three different pathways beginning from a common N-hydrazonyl radical, which evolves through a domino carboamination/dearomatization, a HAT process, or a photoinduced radical Smiles rearrangement to afford diverse tetrahydropyridazines. All reactions are carried out in very mild conditions, and the quite inexpensive [Ru(bpy)3]Cl2 is used as the catalyst. Preliminary mechanism studies are presented, among them luminescence and electrochemical characterization of the involved species. Computational studies allow to rationalize the mechanism in accord with the experimental findings.
One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization-Methylation
Latham, Daniel E.,Polidano, Kurt,Williams, Jonathan M. J.,Morrill, Louis C.
supporting information, p. 7914 - 7918 (2019/10/16)
A one-pot iron-catalyzed conversion of allylic alcohols to α-methyl ketones has been developed. This isomerization-methylation strategy utilized a (cyclopentadienone)iron(0) carbonyl complex as precatalyst and methanol as the C1 source. A diverse range of allylic alcohols undergoes isomerization-methylation to form α-methyl ketones in good isolated yields (up to 84% isolated yield).