101137-70-6Relevant articles and documents
TMSOTf-mediated approach to 1,3-oxazin-2-one skeleton through one-pot successive reduction-[4 + 2] cyclization process of imides with ynamides
Zhang, Chen-Chen,Huo, Zhi-Peng,Tang, Mei-Lin,Liang, Yong-Xi,Sun, Xun
supporting information, (2021/03/15)
A one-pot approach to access functionalized 1,3-oxazin-2-one skeleton has been developed through successive reduction and subsequent [4 + 2] cyclization process of N-Boc lactams with ynamides by TMSOTf. As a result, a number of five to seven membered ring fused bicyclic [1,2-c][1,3]oxazin-1-ones 12a-m and tricyclic derivatives 13a-f were obtained in moderate to excellent yields with excellent regioselectivities. Moreover, linear N-Boc amides 9a-e were also amenable to this transformation, and the desired 3,4-dihydro-1,3-oxazin-2-ones 14a-m were readily achieved in moderate yields with excellent regioselectivities.
Acyclic ketene aminal phosphates derived from N,N-diprotected acetamides: stability and cross-couplings
Simas, Alessandro B.C.,de Sales, Daniel L.,Pais, Karla C.
experimental part, p. 6977 - 6980 (2010/02/27)
The synthesis of a stable ketene aminal phosphate (α-phosphoryloxy enecarbamate) derived from N,N-diprotected acetamide, bearing two different removable protecting groups, is disclosed. This synthetic intermediate underwent successful palladium-catalyzed cross-coupling reactions to afford functionalized enynes and dienes.
A Simple Method for tert-Butoxycarbonylation of Amides
Grehn, Leif,Gunnarsson, Kerstin,Ragnarsson, Ulf
, p. 745 - 750 (2007/10/02)
The tert-butoxycarbonyl (Boc) function was conveniently introduced onto the amide nitrogen in several secondary amides using di-tert-butyl dicarbonate in dry acetonitrile with 4-dimethylaminopyridine as catalyst.Carboxamides with different acyl groups such as formyl, acetyl and benzoyl are presented as well as derivatives of carbamic acid.Examples also include other amide types: sulfonamide, sulfenamide and phosphinamide which were all smoothly converted to the corresponding Boc derivatives under these conditions.The yields were generally excellent and the resulting Boc analogues stable compounds which could be stored for months under ordinary conditions.Some stereochemical and structural aspects of this acylation are also discussed.Bulky substituents in the proximity of the amide moiety significantly retarded the reaction and in some cases no product was detected.For one compound with an activated methine group, C acylation was observed.
