54567-10-1Relevant articles and documents
Photoinduced Oxidative Formylation of N,N-Dimethylanilines with Molecular Oxygen without External Photocatalyst
Yang, Shuai,Li, Pinhua,Wang, Zhihui,Wang, Lei
supporting information, p. 3386 - 3389 (2017/07/15)
A photoinduced oxidative formylation of N,N-dimethylanilines with molecular oxygen in the absence of an external photocatalyst was developed and provided the corresponding formamides in good yields under mild reaction conditions. Investigations indicated that both the starting material and product act as photosensitizers and that 1O2 coexists with O2?- during the reaction through energy transfer and single electron transfer process.
Silver-Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone-Fused Carbo- and Heterocycles
Hu, Zhongyan,Dong, Jinhuan,Men, Yang,Lin, Zhichen,Cai, Jinxiong,Xu, Xianxiu
supporting information, p. 1805 - 1809 (2017/02/05)
A silver-catalyzed chemoselective [4+2] annulation of aryl and heteroaryl isocyanides with α-substituted isocyanoacetamides was developed for the facile and efficient synthesis of 2-aminoquinolones, naphthyridines, and phenanthrolines. A mechanism for this multistep domino reaction is proposed on the basis of a13C-labeling experiment, according to which an unprecedented chemoselective heterodimerization of two different isocyanides generates an α-amidoketenimine intermediate, which undergoes 1,3-amino migration to form an α-imidoylketene, followed by 6 π electrocyclization.
Chemoselective double annulation of two different isocyanides: Rapid access to trifluoromethylated indole-fused heterocycles
Gao, Yuelei,Hu, Zhongyan,Dong, Jinhuan,Liu, Jun,Xu, Xianxiu
supporting information, p. 5292 - 5295 (2017/11/06)
An unprecedented chemoselective double annulation of α-trifluoromethylated isocyanides with o-acylaryl isocyanides has been developed. This new reaction provides a rapid, efficient, and complete atom-economic strategy for the synthesis of trifluoromethylated oxadiazino[3,2-α]indoles in a single operation from readily available starting materials. Isocyanide insertion into C=O double bonds is disclosed for the first time as indicated by the results of 18O-labeling experiment. A mechanism for this domino reaction is proposed involving chemoselective heterodimerization of two different isocyanides, followed by indole-2,3-epoxide formation and rearrangement.
Isocyanide cyclization reactions: 4-methylene-4H-benzo[d][1,3]oxazine, 3-benzyl-4-methylene-3,4-dihydroquinazolines and 3-(4-benzyl)-3H-quinazolin-4- ones - Experiment and theory
Neue, Benedikt,Reiermann, Ralph,Froehlich, Roland,Wibbeling, Birgit,Bergander, Klaus,Wuerthwein, Ernst-Ulrich
, p. 4944 - 4952 (2013/08/23)
2-Isocyanoacetophenone (3a) was found to be an easily accessible starting material for the unexpected formation of various heterocyclic systems. Thus, a hitherto unknown rather unstable 4-methylene-4H-benzoxazine derivative 4, which could be characterized by NMR spectroscopy, was formed in situ by the reaction of 3a in the presence of weak acids. In the presence of benzylamines, a new class of 3,4-dihydroquinazoline derivatives 6 and their oxidation products, quinazolin-4-ones 9, were obtained. The starting materials and products were completely characterized by spectroscopic and X-ray analysis. The scope and limitations of these cyclization reactions were investigated under various reaction conditions. High-level quantum chemical calculations were carried out to elucidate the mechanisms leading to scaffolds 4 and 6. The calculations suggest that the formation of 4 and 6 involves the generation of an unusual six-membered N-heterocyclic carbene or its C-protonated form as a reaction intermediate, followed by tautomerisation. This mechanism might also be applicable to other isocyanide cyclization reactions. Copyright
Selective iodine-catalyzed intermolecular oxidative amination of C(sp 3)-H bonds with ortho-carbonyl-substituted anilines to give quinazolines
Yan, Yizhe,Zhang, Yonghui,Feng, Chengtao,Zha, Zhenggen,Wang, Zhiyong
experimental part, p. 8077 - 8081 (2012/08/29)
Access to quinazolines: The selective amination of C(sp3)-H bonds adjacent to nitrogen or oxygen atoms of N-alkylamides, ethers, or alcohols with ortho-carbonyl-substituted anilines constitutes the first step in a tandem annulation that leads to quinazolines in good to excellent yields (see scheme; NIS=N-Iodosuccinimide, TBHP=tert-butyl hydroperoxide). The selectivity of the amination of primary and secondary C-H bonds is also noteworthy (left: >3:1, right: >99:1). Copyright
Indium-catalyzed N -formylation of amines under solvent-free conditions
Kim, Joong-Gon,Jang, Doo Ok
experimental part, p. 1231 - 1234 (2010/07/08)
We have developed a simple, mild method for N-formylation of a wide variety of amines in the presence of indium metal as a catalyst under solvent-free conditions. This reaction is applicable to the chemoselective N-formylation of amino groups and -amino acid esters without epimerization. Georg Thieme Verlag Stuttgart.
One-pot synthesis of quinoline-2(1H)-thiones from 2-isocyanostyrenes via electrocyclic reaction of the corresponding 2-isothiocyanatestyrenes
Kobayashi, Kazuhiro,Fujita, Seiki,Fukamachi, Shuhei,Konishi, Hisatoshi
experimental part, p. 3378 - 3382 (2010/02/28)
The reaction of a-substituted 2-isocyanostyrenes, which could be readily prepared from commercially available 2-aminophenyl ketones or 2-aminobenzonitriles, with sulfur in the presence of a catalytic amount of selenium proceeded smoothly to give the corre
A remarkably simple N-formylation of anilines using polyethylene glycol
Das, Biswanath,Krishnaiah, Maddeboina,Balasubramanyam,Veeranjaneyulu, Boyapati,Nandan Kumar
, p. 2225 - 2227 (2008/09/18)
N-Formylation of anilines has efficiently been carried out at room temperature in excellent yields by treatment with formic acid in polyethylene glycol (PEG-400). No additional solvent and catalyst are required.
A convenient synthesis of quinolines by reactions of o-isocyano-β- methoxystyrenes with nucleophiles
Kobayashi, Kazuhiro,Yoneda, Keiichi,Miyamoto, Kazuna,Morikawa, Osamu,Konishi, Hisatoshi
, p. 11639 - 11645 (2007/10/03)
2,4-Disubstituted quinolines have been synthesized by reactions of o-isocyano-β-methoxystyrenes, which can be easily prepared from commercially available o-aminophenyl ketones in three steps, with alkyl(or aryl)lithiums in generally good yields. Subsequently, o-isocyano-β- methoxystyrenes have also proved to react efficiently with lithium dialkylamides to afford the corresponding 4-substituted N,N-dialkylquinolin-2-amines in satisfactory yields. Graphical Abstract.
One pot conversion of azido arenes to N-arylacetamides and N-arylformamides: Synthesis of 1,4-benzodiazepine-2,5-diones and fused [2,1-b]quinazolinones
Kamal, Ahmed,Ramana, A. Venkata,Reddy, K. Srinivasa,Ramana, K. Venkata,Hari Babu,Prasad, B. Rajendra
, p. 8187 - 8190 (2007/10/03)
Sodium iodide in acidic media has been employed for the synthesis of N-arylformamides and N-arylacetamides. The NaI/acetic acid reagent system has also been extended for the synthesis of 1,4-benzodiazepine-2,5-diones, pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones, and fused [2,1-b]quinazolinones.
