40731-28-0Relevant academic research and scientific papers
Method for preparing 2-nitroindole derivative
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Paragraph 0037, (2018/11/04)
The invention discloses a method for preparing a 2-nitroindole derivative. The pyridine methylindole is taken as an initiator, the raw materials are easily available, and the types are wide; the product obtained by the method has the advantages of various
Addition, Substitution, and Deoxygenation Reactions of α-Phenyl-β-nitrostyrenes with the Anions of Thiols and Diethyl Phosphite: Formation of Indoles by Reaction with Ethyl Phosphites
Russell, Glen A.,Yao, Ching-Fa,Tashtoush, Hasan I.,Russell, June E.,Dedolph, Douglas F.
, p. 663 - 669 (2007/10/02)
Reaction of excess RS- (R=Ph, t-Bu) with Ph2C=C(SPh)NO2 in Me2SO form Ph2C=CHSR via conversion of the initial Michael-type adducts into Ph2C(SR)CH=NO2- and Ph2C=CHNO2.In a similar fashion, reaction of (EtO)2PO- with Ph2C=C(SPh)NO2 forms initially mainly PhSP(O)(OEt)2 and Ph2CCH=NO2-, which upon acidic workup will yield the nitroalkane or the Nef reaction product, Ph2CCHO.The reaction of (EtO)2PO- with Ph2C=C(SPh)NO2 also produces Ph2CCN via a Perkow-type reaction of the Michael adduct to yield Ph2CCH=N(O)OP(O)(OEt)2 as an intermediate.The nitrile is also formed from Ph2CCH(NO2)2 with (EtO)2PO- in (EtO)2P(O)H or Me2SO at 30 deg C and in >95percent yield by the reaction of (EtO)3P with Ph2CCH(NO2)2 at 150 deg C.Reaction of Ph2C=CHNO2 or Ph2CCH2NO2 with excess (EtO)PO- in Me2SO or (EtO)2P(O)H forms 3-(diethoxyphosphinyl)-2,2-diphenylaziridine by a process postulated to involve Ph2C=CHN(O-)OP(O)(OEt)2, Ph2C=CHNOP(O)(OEt)2-, and 2,2-diphenyl-2H-azirine.Similarly, Ph2C=C(SBu-t)NO2 and (EtO)2PO- give 3-(tert-butylthio)-2,2-diphenyl-2H-azirine in Me2SO or 2-(tert-butylthio)-3-phenylindole in (EtO)2P(O)H solution.Deoxygenation of Ph2C=C(X)NO2 to form the 2-X-3-phenylindoles occurs in high yield at 150 deg C in (EtO)3P with X=H, PhS, or t-BuS while 2-nitrro-3-phenylindole is formed from Ph2C=C(NO2)2 in (EtO)2P(O)H at 150 deg C.
