23343-06-8Relevant articles and documents
Hydride transfer reactions of 5-(2-alkohybenzylidene) barbituric acids: Synthesis of 2,4,6-trioxoperhydropyrimidine-5-spiro-3′-chromanes
Krasnov, Konstantin A.,Dorovatovskii, Pavel V.,Zubavichus, Yan V.,Timofeeva, Tatiana V.,Khrustalev, Victor N.
, p. 542 - 549 (2017/01/12)
The thermal cyclization of 5-(2-phenoxymethylphenyl-methylene)barbituric acid and its derivatives affords 2,4,6-trioxoperhydropyrimidine-5-spiro-3′-chromanes. The reactions require no catalysts and proceed at temperatures from 118 to 240?°C depending on the substrate activity. These cyclization reactions are analogous to T-reactions of tertiary amines involving the hydride transfer.
A cascade Claisen rearrangement/o-quinone methide formation/electrocyclization approach to 2H-chromenes
Song, Liyan,Huang, Fang,Guo, Liwen,Ouyang, Ming-An,Tong, Rongbiao
supporting information, p. 6021 - 6024 (2017/07/10)
A new approach has been developed for the synthesis of 8-substituted 2H-chromenes, featuring a novel cascade aromatic Claisen rearrangement/o-quinone methide formation/6π-electrocyclization. This new method was demonstrated with 28 examples tolerating different substitutions at alkenes, allylic and aromatic ring and with total syntheses of three 2H-chromene natural products.
The Synthesis of 5-Amino-dihydrobenzo[b]oxepines and 5-Amino-dihydrobenzo[b]azepines via Ichikawa Rearrangement and Ring-Closing Metathesis
Chwastek, Monika,Pieczykolan, Micha?,Stecko, Sebastian
, p. 9046 - 9074 (2016/10/17)
The combination of Ichikawa's rearrangement and a ring-closing metathesis reaction of allyl carbamates is presented as a method for the preparation of 5-amino-substituted 2,5-dihydro-benzo[b]oxepines, 2,5-dihydro-benzo[b]azepines, and 2,5-dihydro-benzo[b]thiepins. It was demonstrated that the use of nonracemic allyl carbamates enables the synthesis of enantioenriched benzo-fused seven-membered heterocycles. Finally, it was shown that further functionalization of the obtained structures allows access to pharmacologically active 5-amino-substituted 2,3,4,5-tetrahydro-1-benzo[b]oxepine scaffolds.