15950-17-1Relevant articles and documents
Selective one-pot N-monomethylation of 2-nitroanilines under PTC conditions
Voskresensky,Makosza
, p. 3523 - 3526 (2000)
Direct PTC methylation of 2-nitroanilines with dimethyl sulfate gave selectively N-monomethylated products. A variety of N-methyl-2-nitroanilines were prepared in this way.
Oxidative Radical Cyclization of N-methyl-N-arylpropiolamide to Isatins via Cleavage of the Carbon-carbon Triple Bond
Liao, Yan-Yan,Gao, Yong-Chao,Zheng, Wenxu,Tang, Ri-Yuan
supporting information, p. 3391 - 3400 (2018/07/31)
A radical cyclization of N-methyl-N-arylpropiolamide to isatins via an oxidative cleavage of a carbon-carbon triple bond has been developed. In the presence of oxone and NaNO2, a variety of N-methyl-N-arylpropiolamides were smoothly transformed into isatins. A nitration reaction proceeded along with the oxidative cyclization; both nitrated and non-nitrated isatins were obtained in a one-pot reaction with moderate to good total yields. This is the first example for the synthesis of isatins via the oxidative radical cleavage of a carbon-carbon triple bond. (Figure presented.).
Amino Azaxylylenes Photogenerated from o-Amido Imines: Photoassisted Access to Complex Spiro-Poly-Heterocycles
Mukhina, Olga A.,Kuznetsov, Dmitry M.,Cowger, Teresa M.,Kutateladze, Andrei G.
supporting information, p. 11516 - 11520 (2015/11/03)
Upon irradiation, cyclic imines containing o-amido groups are shown to produce reactive intermediates, amino azaxylylenes, which undergo intramolecular cycloadditions to tethered unsaturated pendants to yield complex N,O-heterocycles having an additional spiro-connected nitrogen heterocyclic moiety. Modular assembly of the photoprecursors allows expeditious increase of the complexity of the target poly-heterocyclic scaffolds with a minimal number of experimentally simple reaction steps. The photocyclization and subsequent postphotochemical transformations are accompanied by an increase of Lovering's fsp3 factor, thus producing unprecedented three-dimensional molecular architectures, and offering extended sampling of chemical space. Rings in three dimensions: Cyclic imines containing an o-amido group undergo excited-state intramolecular proton transfer to generate amino azaxylylenes. The amino azaxylylenes undergo intramolecular cycloadditions to tethered unsaturated pendants to yield complex heterocyclic three-dimensional molecular architectures.