49830-37-7Relevant articles and documents
Total syntheses of (±)-massadine and massadine chloride
Su, Shun,Seiple, Ian B.,Young, Ian S.,Baran, Phil S.
, p. 16490 - 16491 (2008)
The total syntheses of the complex pyrrole-imidazole alkaloids (±)-massadine and (±)-massadine chloride is described using a carefully orchestrated sequence of manipulations on highly polar and structurally complex intermediates. Key to the completion of this synthetic endeavor was the exploration of a unique and chemoselective method to oxidize unprotected guanidines under aqueous conditions in air. This oxidation has been optimized and applied to a selection of spirocyclic guanidines of varying complexity. Additionally, the 3,7-epi analogues of these interesting natural products have been synthesized and fully characterized. Copyright
Photoreactive fused aziridinylpiperazines on the background of 4-substituted chalcones and their benzimidazolic analogs
Kotlyar, Volodymyr M.,Kolomoitsev, Oleksii O.,Nikolaievskyi, Dmytro V.,Pedan, Polina I.,Chumak, Andrii Yu,Orlov, Valery D.,Shishkina, Svitlana V.,Doroshenko, Andrey O.
, p. 741 - 746 (2019/01/10)
The reaction of bromo-substituted chalcones with various diamino-compounds leads to the fused heterocyclic products, aziridinylpiperazines, exhibiting photoreactivity in the crystalline state. Crystals of 4-nitrosubstituted compounds of this family change their color from yellowish to deep violet-blue, 4-cyanosubstituted ones – from yellowish to pink at UV irradiation. Discussion on the mechanism of this phototransformation is still in progress, however, several facts points to the free radial nature of the photogenerated colored semi-products stabilized only by crystalline state of the irradiated samples. Formation of a mixture of positional isomers at interaction of bromo-chalcones with asymmetric diamines of aliphatic/alicyclic or aromatic series at synthesis of the title compounds is of significant interest as well.
A Sustainable, Semi-Continuous Flow Synthesis of Hydantoins
Vukeli?, Stella,Koksch, Beate,Seeberger, Peter H.,Gilmore, Kerry
supporting information, p. 13451 - 13454 (2016/09/13)
Hydantoins are an important class of heterocycles with applications in pharmacy, agriculture, and as intermediates in organic synthesis. Traditional synthetic procedures to access hydantoins are target oriented with multiple synthetic steps and often use reagents that are not commercially available or sustainable. Herein, an efficient process is described for accessing hydantoins starting from commercially available amines using consecutive gas–liquid transformations (oxygen, carbon dioxide). This semi-continuous process produced ten benzylic/aliphatic hydantoins in good overall yields (52–84 %).