99137-13-0Relevant academic research and scientific papers
Transition-metal-free multinitrogenation of amides by C-C bond cleavage: A new approach to tetrazoles
Li, Lian-Hua,Li, Ying-Xiu,Liang, Yong-Min,Niu, Zhi-Jie
supporting information, p. 11148 - 11151 (2020/04/22)
A metal-free brand-new one-pot multinitrogenation of amides for the chemo- A nd regioselective synthesis of 1,5-disubstituted tetrazoles has been developed. By means of electrophilic amide activation, and further C-C bond cleavage and rearrangement, a diverse set of functionalized 1,5-DST derivatives were selectively constructed under mild conditions. As showcased in the mechanisms, the chemoselectivity is easily switched by the selection of the starting materials in the reaction.
Direct C-H arylation and alkenylation of 1-substituted tetrazoles: Phosphine as stabilizing factor
Spulak, Marcel,Lubojacky, Richard,Senel, Petr,Kunes, Jiri,Pour, Milan
experimental part, p. 241 - 244 (2010/04/06)
(Chemical Equation Presented) Direct arylation and alkenylation of 1-substituted tetrazoles was achieved via Pd catalysis in the presence of CuI and Cs2CO3. Unlike the related reactions of imidazoles and purines, phosphine ligand was
Improved Schmidt synthesis of 1,5-disubstituted 1H-tetrazoles from ketones
Suzuki,Hwang,Nakaya,Matano
, p. 1218 - 1220 (2007/10/02)
On treatment with an excess of sodium azide in the presence of titanium(IV) chloride in boiling acetonitrile, both aliphatic and aromatic ketones are smoothly converted to 1,5-disubstituted 1H-tetrazoles in high yields.
Intramolecular Reaction Between Nitro and Carbodi-imide Groups; A New Synthesis of 2-Arylbenzotriazoles
Houghton, Peter G.,Pipe, David F.,Rees, Charles W.
, p. 1471 - 1480 (2007/10/02)
1-(2-Nitrophenyl)-5-phenyltetrazole (5b) decomposes when heated to give nitrogen, carbon dioxide, and 2-phenylbenzotriazole (6) in high yield.This new molecular rearrangement proceeds via 2-nitrophenyl(phenyl)carbodi-imide (8).Other precursors of this carbodi-imide, i.e. oxadiazolone (10), oxadiazolethione (11), oxathiadiazole 2-oxide (12), and the aminimide (16), and carbodi-imide itself, all give 2-phenylbenzotriazole (6) on thermolysis, the last three in high yield.This reaction is general for diarylcarbodi-imides with an ortho nitro group, and their precursors, and it provides a useful new route to 2-arylbenzotriazoles.A sequence of electrocyclic ring closing and opening reactions (Scheme 5) is proposed as the mechanism of this process.The key intermediate, 2-phenyl-1,2,4-benzotriazin-3-one 1-oxide (19) has been isolated from a careful thermolysis of (12) in toluene; in solution it is in reversible equlibrium with the ring-opened form (20).This new nitro-carbodi-imide group interaction has been extended to the more stable nitrobiphenyl(phenyl)carbodi-imide (25) and nitronaphthyl(phenyl)carbodi-imide (24) which, on flash vacuum pyrolysis, give benzimidazophenanthridine (29) and benzindazole 1-oxide (32) respectively, in new rearrangements.
