119119-74-3Relevant academic research and scientific papers
Copper-catalyzed rearrangement of (Z)-propynal hydrazones via N-N bond cleavage
Nakamura, Itaru,Shiraiwa, Naozumi,Kanazawa, Ryo,Terada, Masahiro
supporting information; experimental part, p. 4198 - 4200 (2010/11/19)
Propynal hydrazones are successfully converted to the corresponding 3-aminoacrylonitriles in the presence of copper catalysts in good to high yields. As an example, (Z)-N-(hex-2-ynylidene)morpholin-4-amine reacted in the presence of 10 mol % Cu(OAc)2 in acetonitrile at 25 °C to afford (E)-3-morpholinohex-2-enenitrile ((E)-2 h) in 77% yield via C-N bond formation and subsequent β-elimination involving cleavage of N-N and C-H bonds.
REACTION OF DICHLOROCARBENE WITH SUBSTITUTED 3,4-DIHYDROISOQUINOLINES AND 1-METHYLENE-1,2,3,4-TETRAHYDROISOQUINOLINES
Khlebnikov, A. F.,Kostikov, R. R.,Shklyaev, V. S.,Aleksandrov, B. B.,Dormidontov, M. Yu.
, p. 909 - 913 (2007/10/02)
Reaction of dichlorocarbene with 3,3-dialkyl-3,4-dihydroisoquinolines results in the formation of gem-dichloroazirinoisoquinolines, which are in turn converted to 3-benzazepinones upon hydrolysis.Reaction of dichlorocarbene with the ethyl ester or amide of (3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-ylidene)acetic acid is accompanied by rearrangement of the intermediate carbene adducts at the enamine C=C bond and results in the formation of a 1-azadiene, 3-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-3-chloroacrylic acid ethyl ester, and a spirolactam, 3,3-dimethyl-3-chlorospiro-5'(2'H)- one, respectively.
E/Z Photoisomerization of 3-Amino-3-phenylprop-2-enenitriles
Chiacchio, Ugo,Musumarra, Giuseppe,Purrello, Giovanni
, p. 1591 - 1594 (2007/10/02)
The E/Z photoisomerization of 3-phenyl-3-(N-substituted amino)- and 3-phenyl-3-(N,N-disubstituted amino)-prop-2-enenitriles was investigated by means of u.v. and 13C n.m.r. spectroscopy.Informative results on the mechanism of the reaction produced by direct irradiation of 3-anilino-3-phenylprop-2-enenitrile were obtained from the different effects of quenchers and heavy atoms.Neither the heavy atoms nor the quenchers had any effect on direct photoisomerisation, which involves only the singlet state, by-passing the triplet state.
