220466-10-4Relevant academic research and scientific papers
Lewis acid-catalyzed or base-promoted regioselective cycloisomerization of N-imidoyl-o-alkynylanilines for synthesis of N-imidoyl-(1-H)-indoles and 4-alkylidene-3,4-dihydroquinazolines
Otani, Takashi,Jiang, Xue,Cho, Kinryo,Araki, Rino,Kutsumura, Noriki,Saito, Takao
supporting information, p. 1483 - 1492 (2015/05/19)
Product selectivity control for the synthesis of imidoylindoles and 4-alkylidenedihydroquinazolines from N-imidoyl-o-alkynylanilines via silver triflate-catalyzed cycloisomerization or tetrabutylammonium fluoride-promoted cyclization is described. The pro
Efficient regioselective synthesis of 3-iodoindole N-carboximidamides and N-carboximidoates by a sequential aza-wittig/iodine induced cyclization
Nie, Yibo,Duan, Zhuan,Ding, Mingwu
, p. 1807 - 1812 (2012/10/29)
3-Iodoindole N-carboximidamides and N-carboximidoates 4 were prepared regioselectively via a sequential aza-Wittig/iodine induced cyclization, starting from easily accessible 2-alkynylphenyl iminophosphorane, isocyanates, various nucleophiles and iodine.
Efficient regioselective synthesis of indole N-carboximidamides and N-carboximidoates by a sequential aza-wittig/Ag(I)-catalyzed cyclization
Huang, Nian-Yu,Liu, Ming-Guo,Ding, Ming-Wu
supporting information; experimental part, p. 6874 - 6877 (2009/12/07)
(Chemical Equation Presented) An efficient Ag(I)-catalyzed regioselective cyclization of (2-alkynylphenyl)guanidine or (2-alkynylphenyl)isourea to indole N-carboximidamides or N-carboximidoates has been developed. The approach has the advantages of high regioselectivity, mild reaction conditions, easily accessible starting materials, and good yields. 2009 American Chemical Society.
A novel heterocumulenic Pauson-Khand reaction of alkynylcarbodiimides: A facile and efficient synthesis of heterocyclic ring-fused pyrrolinones
Saito, Takao,Shiotani, Masahiro,Otani, Takashi,Hasaba, Satoshi
, p. 1045 - 1048 (2007/10/03)
The first examples of the heterocumulenic Pauson-Khand reaction are described. Alkynylcarbodiimides undergo an intramolecular Pauson-Khand cycloaddition upon heating in the presence of Mo(CO)6 and DMSO to afford 4,5-dihydro-1H-pyrrolo[2,3-b]pyrrolin-2-ones and 1H-pyrrolo[2,3-b]indol-2-ones.
Biradicals from thermolysis of N-[2-(1-alkynyl)phenyl]-N'- phenylcarbodiimides and their subsequent transformations to 6H-indolo[2,3- b]quinolines
Shi, Chongsheng,Zhang, Quan,Wang, Kung K.
, p. 925 - 932 (2007/10/03)
Thermolysis of the carbodiimide 9a in γ-terpinene at 138 °C produced 2-(phenylamino)quinoline (11a, 49%) and the parent 6H-indolo[2,3-b]quinoline (14a, 16%). Apparently, 11a was produced via the biradical 10a followed by hydrogen-atom abstraction from γ-terpinene. A two-step biradical pathway through 12a or a one-step intramolecular Diels-Alder reaction could furnish 13a, which then underwent tautomerization to give 14a. With the carbodiimide 9b having a trimethylsilyl substituent at the acetylenic terminus, thermolysis in refluxing p-xylene at 138 °C produced the 6H-indolo[2,3- b]quinoline 14b (86%) exclusively. Treatment of 14b with 6 N NaOH in refluxing ethanol then furnished 14a in 92% yield. Similarly, the 6H- indolo[2,3-b]quinolines 14c-f were obtained from thermolysis of the carbodiimides 9c-f. The use of the aza-Wittig reaction between 4- methoxyphenyl isocyanate and the iminophosphoranes 2d and 2f to produce the corresponding carbodiimides followed by thermolysis furnished the 6H- indolo[2,3-b]quinolines 16d and 16f having a methoxy substituent at the C-2 position. Thermolysis of the carbodiimides 25a and 25b produced 26a and 26b having two indoloquinoline units connected at the 11 and 11' positions with either a three-carbon or a five-carbon tether. Using 1,4-phenylene diisocyanate for the aza-Wittig reaction with 2 equiv of the iminophosphorane 2g followed by thermolysis furnished 31 (66%) having two indoloquinoline units incorporated in the seven fused rings.
