17605-06-0Relevant articles and documents
Thermolysis of geminal diazides: Reagent-free synthesis of 3-hydroxypyridines
Erhardt, Hellmuth,Kunz, Kevin A.,Kirsch, Stefan F.
, p. 178 - 181 (2017)
An operationally simple protocol for the rapid and efficient construction of highly substituted 3-hydroxypyridines is presented. The thermally induced cyclization of easily constructed geminal diazides derived from β- ketoesters having an additional olefin moiety affords the title compounds in yields up to 97% under reagent-free conditions. The new method allows for the synthesis of preparative quantities of material. Additionally, the synthetic utility of the pyridine products for the synthesis of valuable heterocycles is described.
Efficient Synthesis of butenolide-medium ring ether hybrids by a [3 + 2] cyclization-ring-closing metathesis strategy
Langer, Peter,Eckardt, Tobias,Stoll, Martin
, p. 2991 - 2993 (2000)
A new strategy for the synthesis of bicyclic γ-alkylidenebutenolides, butenolide-medium ring ether hybrids, is reported which involves Me3-SiOTf-catalyzed cyclization of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with oxalyl chloride, Mitsunobu reaction, and subsequent ring-closing metathesis.
A Suite of “Minimalist” Photo-Crosslinkers for Live-Cell Imaging and Chemical Proteomics: Case Study with BRD4 Inhibitors
Pan, Sijun,Jang, Se-Young,Wang, Danyang,Liew, Si Si,Li, Zhengqiu,Lee, Jun-Seok,Yao, Shao Q.
, p. 11816 - 11821 (2017)
Affinity-based probes (AfBPs) provide a powerful tool for large-scale chemoproteomic studies of drug–target interactions. The development of high-quality probes capable of recapitulating genuine drug–target engagement, however, could be challenging. “Mini
Pd(OAc)2-catalyzed orthogonal synthesis of 2-hydroxybenzoates and substituted cyclohexanones from acyclic unsaturated 1,3-carbonyl compounds
Miyagi, Toshinori,Okada, Sho,Tada, Naoya,Sugihara, Masahiro,Kagawa, Natsuko,Takabatake, Tetsuhiko,Toyota, Masahiro
supporting information, p. 1653 - 1657 (2019/05/29)
A Pd-catalyzed orthogonal synthesis of substituted 2-hydroxybenzoates and substituted cyclohexanones was developed for the first time. The substituted 2-hydroxybenzoates were obtained from acyclic unsaturated 1,3-carbonyl compounds using a combination of catalytic Pd(OAc)2 and Cu(OAc)2. On the other hand, the substituted cyclohexanones were produced from similar substrates via catalytic Pd(OAc)2 and hydrogen chloride. Each transformation was clean, easy to work up, provided the desired compounds in good purities, and did not require column chromatography purification.
General [4 + 1] Cyclization Approach to Access 2,2-Disubstituted Tetrahydrofurans Enabled by Electrophilic Bifunctional Peroxides
Gao, Min,Zhao, Yukun,Zhong, Chen,Liu, Shengshu,Liu, Pengkang,Yin, Qi,Hu, Lin
supporting information, p. 5679 - 5684 (2019/08/01)
A general [4 + 1] cyclization reaction of carbonyl nucleophiles with 2-iodomethylallyl peroxides, which function as unique electrophilic oxygen synthons, for the synthesis of a broad range of 2,2-disubstituted tetrahydrofurans is achieved under operationally simple conditions. The unprecedented asymmetric version of such reaction is also realized via chiral auxiliary-assisted cyclization, thus providing a distinct approach to access chiral tetrahydrofurans with high diastereoselectivities. The new method can be applied to the synthesis of core structure of posaconazole drug.
