139347-76-5Relevant academic research and scientific papers
Nucleophilic Tele-substitution in 2-Chloro-3-formylindoles via Ring Opening-Ring Closure
Pluta, Krystian,Andersen, Kim V.,Jensen, Frank,Becher, Jan
, p. 1583 - 1584 (1988)
2-Chloro-3-formylindoles give 5-azido-3-cyanoindoles on reaction with an excess of sodium azide in dimethylsulphoxide, as a result of a ring opening-ring closure with concomitant nucleophilic substitution at the 5-position in the indole ring; the X-ray cr
Chemospecific synthesis of 2-acetoxyindole-3-carbonitriles catalyzed by Cu(acac)2
Mo, Shanyan,Tu, Jianzhuo,Xu, Jiaxi
, p. 1773 - 1778 (2017/03/22)
A chemospecific one-pot synthesis of easily isolable 2-acetoxyindole-3-carbonitriles was described. The intermediate 2-oxindole-3-carbonitriles successfully prepared from 2-cyano diazoacetanilides without isolation were treated with acetyl chloride and tr
Isoindolinone formamide skeleton-containing boron bifluoride complex and preparing method thereof
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Paragraph 0026, (2016/10/09)
The invention provides an indoline-2-one-3-formamide key skeleton-containing boron bifluoride complex and a preparing method thereof. The indoline-2-one-3-formamide key skeleton-containing boron bifluoride complex is obtained by cyclizing an N-aryl-2-diaz
Metal-free synthesis of 2-oxindoles via PhI(OAc)2-mediated oxidative C-C bond formation
Lv, Jinglei,Zhang-Negrerie, Daisy,Deng, Jun,Du, Yunfei,Zhao, Kang
, p. 1111 - 1119 (2014/03/21)
The series of 3-monofunctionalized 2-oxindoles 2 were conveniently synthesized from reactions between anilide 1 and phenyliodine(III) diacetate (PIDA) through hypervalent iodine mediated C(sp2)-C(sp2) bond formation followed by a subsequent deacylation reaction. This metal-free method, shown to provide direct access to an important oxindole intermediate, could be applied to the total synthesis of naturally occurring horsfiline.
Azide Ring-Opening-Ring-Closure Reactions and Tele-substitutions in Vicinal Azidopyrazole-, Pyrrole- and Indolecarboxaldehydes
Becher, Jan,Joergensen, Per Lauge,Pluta, Krystian,Krake, Niels J.,Faelt-Hansen, Birgitte
, p. 2127 - 2134 (2007/10/02)
5-Chloro-1-methylpyrazole-4-carboxaldehydes 1 react with excess sodium azide in dimethyl sulfoxide to produce a mixture of 1-azidomethyl-4-cyanopyrazoles 2 and 4-cyano-5-hydroxy-1-methylpyrazoles 3.Application of this reaction to the corresponding 5-chloro-1-phenylpyrazole-4-carboxaldehydes 5 gave 4-cyano-5-hydroxy-1-phenyl-pyrazoles 7 as the sole products in high yields.Likewise, 2-aryl-5-chloro-1-methylpyrrole-3,4-dicarboxaldehydes 9 rearranged to 2-aryl-4-cyano-5-hydroxy-1-methylpyrrole-3-carboxaldehydes 10 in high yields.In the indole series, treatment of 1-aryl-2-chloroindole-3-carboxaldehydes 11 with NaN3 yielded a mixture of 1-aryl-3-cyano-2(3H)-indolones 13 and 1-aryl-5-azido-3-cyanoindoles 12, both products resulting from a ring-opening-ring-closure reaction with concomitant nucleophilic tele-substitution at the 5-position of the indole ring.
