6403-55-0Relevant academic research and scientific papers
Iridium-Catalyzed Direct Cyclization of Aromatic Amines with Diols
Minakawa, Maki,Watanabe, Kouichi,Toyoda, Satoru,Uozumi, Yasuhiro
supporting information, p. 2385 - 2389 (2018/11/23)
We developed an environmentally friendly iridium-catalyzed direct cyclization of aromatic amines with diols that generates the corresponding N-heterocyclic compounds with water as the sole by-product. Thus, under conditions of 165 °C for 18 hours, the direct cyclization of N -methylanilines with 1,3-propanediol by using an IrCl 3 catalyst with rac -BINAP as a ligand in mesitylene afforded the corresponding tetrahydroquinoline derivatives with yields ranging from 73 to 83%. Under similar reaction conditions, direct cyclization of anilines with 1,3-propanediol produced the corresponding tetrahydrobenzoquinolizine derivatives with yields ranging from 26 to 76%.
Amino-Claisen Rearrangement. IV. Quaternary Amino-Claisen Rearrangement of N-Allyljulolidinium Derivatives
Katayama, Hajime,Ohkoshi, Mitsuko,Kaneko, Kimiyoshi
, p. 1770 - 1779 (2007/10/02)
The amino-Claisen rearrangements of 9-unsubstituted and 9-substituted N-allyljulolidinium halides were investigated.The former compounds can be regarded as aniline derivatives in which the two ortho sites are occupied.In the latter compounds, the two ortho positions and the para position are all blocked.N-Allyljulolidinium halides rearranged into 9-allyljulolidine.However, 9-substituted N-allyljulolidinium halides gave 8-allyl-9-substituted julolidines.This meta rearrangement constitutes the first reported example of meta amino-Claisen rearrangement.The reaction pathways can be rationalized in terms of a combination of and sigmatropic rearrangements.Keywords - amino-Claisen rearrangement; meta-rearrangement; N-allyljulolidinium halide; 9-substituted-N-allyljulolidinium halide; 9-allyljulolidine; 8-allyl-9-substituted julolidine; sigmatropic rearrangement; sigmatropic rearrangement
Synthesis of Julolidines from Anilines
Katayama, Hajime,Abe, Eiichi,Kaneko, Kimiyoshi
, p. 925 - 926 (2007/10/02)
Substituted julolidines were prepared by a single step of reactions from substituted anilines.
Amino-Claisen Rearrangement of N-Allyljulolidinium Halides
Katayama, Hajime
, p. 1009 - 1011 (2007/10/02)
Amino-Claisen rearrangement of 4-allyljulolidinium halides and 4-allyl-9-substituted-julolidinium bromides gave 9-allyljulolidines and 8-allyl-9-substituted julolidines respectively, the latter of which is the first example of meta-amino-Claisen rearrangement to be reported.
