99532-56-6Relevant academic research and scientific papers
CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene intermediates
Liao, Zhen-Yuan,Liao, Pen-Yuan,Chien, Tun-Cheng
, p. 14404 - 14407 (2016/12/23)
CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides was initiated by the formation of Cu-acetylide to trigger N-CN bond cleavage of the N-sulfonylcyanamide moiety followed by CN migration to form a β-cyano Cu-vinylidene intermediate. Subsequently, the indole ring closure furnished the corresponding 1-sulfonyl-3-cyanoindoles.
One-pot transformation of methylarenes into aromatic nitriles with inorganic metal-free reagents
Kawagoe, Yuhsuke,Moriyama, Katsuhiko,Togo, Hideo
, p. 4115 - 4122 (2014/07/08)
Various methylarenes were transformed into the corresponding aromatic nitriles in good to moderate yields by the treatment with aq. HBr and aq. H 2O2, followed by reaction with molecular iodine and aq. ammonia in a one-pot procedure. The present reaction is a useful, practical, transition-metal-free, and organic-reagent-free method for the preparation of aromatic nitriles from methylarenes. Various methylarenes were treated with aq. HBr and aq. H2O2 under warming conditions and/or irradiation conditions, followed by the reaction with molecular iodine and aq. ammonia, to provide the corresponding aromatic nitriles, in a one-pot procedure. The present reaction was carried out under metal-free and organic-reagent-free conditions. Copyright
Direct oxidative conversion of methylarenes into aromatic nitriles
Tsuchiya, Daisuke,Kawagoe, Yuhsuke,Moriyama, Katsuhiko,Togo, Hideo
supporting information, p. 4194 - 4197 (2013/09/12)
A variety of methylarenes were successfully converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with NBS or DBDMH in the presence of a catalytic amount of AIBN or BPO, followed by the reaction with molecular iodine in aq NH3 in a one-pot procedure. The present reaction is a useful and practical transition-metal-free method for the preparation of aromatic nitriles from methylarenes.
A facile synthesis of 1-phenylsulfonyl-3-substituted-2-cyanoindoles, 1-phenylsulfonyl-2-methyl-3-cyanoindoles, and bifunctional 1- phenylsulfonylindoles
Jaisankar, Pichamuthu,Srinivasan
, p. 2413 - 2417 (2008/03/13)
A facile 'one-pot' introduction of the cyano group into the 2/3-position of indole has been developed from the corresponding aldehydes using anhydrous aluminum chloride and sodium azide. Georg Thieme Verlag Stuttgart.
Carbopalladation of nitriles: Synthesis of 2,3-diarylindenones and polycyclic aromatic ketones by the Pd-catalyzed annulation of alkynes and bicyclic alkenes by 2-iodoarenenitriles
Pletnev, Alexandre A.,Tian, Qingping,Larock, Richard C.
, p. 9276 - 9287 (2007/10/03)
2-Iodobenzonitrile, its derivatives, and various heterocyclic analogues undergo palladium(O)-catalyzed annulation onto diarylacetylenes or bicyclic alkenes to afford 2,3-diarylindenones and polycyclic aromatic ketones in very good to excellent yields. This reaction represents one of the first examples of the addition of an organopalladium moiety to the carbon-nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed.
Palladium-catalyzed cyanation of aryl and heteroaryl iodides with copper(i) cyanide
Sakamoto, Takao,Ohsawa, Kazutoshi
, p. 2323 - 2326 (2007/10/03)
The palladium-catalyzed cyanation of aryl and heteroaryl iodides or bromides using copper(i) cyanide as a cyano group source afforded the corresponding aryl and heteroaryl cyanides in good yields.
A Convenient Synthesis of 3-Acylindoles via Friedel-Crafts Acylation of 1-(Phenylsulfonyl)indole. A New Route to Pyridocarbazole-5,11-quinones and Ellipticine
Ketcha, Daniel M.,Gribble, Gordon W.
, p. 5451 - 5457 (2007/10/02)
A Friedel-Crafts acylation of 1-(phenylsulfonyl)indoles (1) with carboxylic acid anhydrides and acid chlorides in the presence of aluminum chloride gives 3-acyl-1-(phenylsulfonyl)indoles (2) in 81-99percent yields.Base hydrolysis converts 2 to 3-acylindoles (3) in 79-96percent yields.The reaction of 1-(phenylsulfonyl)indole (1a) with oxalyl chloride gives acid chloride 2h, which is converted to 3-cyanoindole (7) in three steps (75percent yield).Although a similar Friedel-Crafts alkylation of 1 was unsuccessful, in some cases the 3-acyl-1-(phenylsulfonyl)indoles 2a,e,f could be reduced to 3-alkyl-1-(phenylsulfonyl)indoles 8a,b,c in nearly quantitative yield with sodium borohydride in trifluoroacetic acid.The acid chloride derived from keto acid 9 did not cyclize to the desired pyridocarbazole-5,11-quinone 24 but rather to chloro keto lactam 10.However, acylation of 1a with acid chloride 22 followed by strong-base-mediated cyclization gives 24.Since quinone 24 has been previously converted to the alkaloid ellipticine 26, this route to 24 represents a new synthesis of ellipticine.Related synthetic schemes give rise to quinones 16 and 20.
