10441-73-3Relevant academic research and scientific papers
Recyclable gallium(III) triflate-catalyzed [4+3] cycloaddition for synthesis of 2,4-disubstituted-3H-benzo[b][1,4]diazepines
Huang, Shi-Gang,Mao, Hai-Feng,Zhou, Shao-Fang,Zou, Jian-Ping,Zhang, Wei
supporting information, p. 6178 - 6180 (2013/10/22)
Simple and efficient Ga(OTf)3-catalyzed [4+3] cycloaddition of 1,3-diarylpropynones and o-phenylenediamines is developed for the preparation of 2,4-disubstituted-3H-benzo[b][1,4]diazepines. The reaction has advantages of using a green solvent, generating a minimal amount of waste, and easy catalyst recycle.
Dissecting alkynes: Full cleavage of polarized C≡C moiety via sequential bis-michael addition/retro-mannich cascade
Roy, Saumya,Davydova, Maria P.,Pal, Runa,Gilmore, Kerry,Tolstikov, Genrikh A.,Vasilevsky, Sergei F.,Alabugin, Igor V.
experimental part, p. 7482 - 7490 (2011/11/30)
The reaction of diaryl ketoalkynes with 1,2-diamino ethane leads to the full scission of the triple bond with the formation of acetophenone and imidazoline fragments. In this transformation, one of the alkyne carbons undergoes formal reduction with the formation of three C-H bonds, whereas the other carbon undergoes formal oxidation via the formation of three C-N bonds (one π and two σ). Computational analysis confirmed that the key fragmentation step proceeds via a six-membered TS in a concerted manner. Both amines are involved in the fragmentation: the N-H moiety of one amine transfers a proton to the developing negative charge at the enolate oxygen, while the other amine provides direct stereoelectronic assistance to the C-C bond cleavage via a hyperconjugative nN → σ*C-C interaction.
Reactions of β-Sulfenyl α,β-Unsaturated Ketones with Guanidine, Amidines and Diamines
Nishio, Takehiko,Tokunaga, Tatsuhiro,Omote, Yoshimori
, p. 405 - 407 (2007/10/02)
β-Sulfenyl α,β-unsaturated ketones 1a-c reacted with guanidine or amidines to give pyrimidine derivatives 3 in 14-76percent yields.Treatment of ketones 1 with diamines such as ethylenediamine and o-phenylenediamine afforded the seven-membered heterocycles, 2,3-dihydro-1,4-diazepine 5 and 2,3-benzo-1,4-diazepines 8a-c.
