61436-87-1Relevant academic research and scientific papers
Visible light driven metal-free intramolecular cyclization: A facile synthesis of 3-position substituted 3,4-dihydroisoquinolin-1(2: H)-one
Zou, Shuai,Geng, Shu,Chen, Lina,Wang, Haitao,Huang, Feng
, p. 380 - 387 (2019/01/10)
A visible-light metal-free photocatalytic synthesis of 3-position substituted 3,4-dihydroisoquinolin-1(2H)-one derivatives under mild conditions in moderate to good yields is described. EosinY Na, an organic dye, which is of low cost and has good availability, is used as the photocatalyst. A wide range of substrates are tolerated and the gram-scale reaction can also proceed smoothly. Mechanistic studies indicate that a plausible free radical process is proposed.
Platinum-catalyzed, one-pot tandem synthesis of indoles and isoquinolines via sequential rearrangement of amides and aminocyclization
Okamoto, Noriko,Takeda, Kei,Yanada, Reiko
supporting information; experimental part, p. 7615 - 7625 (2011/02/25)
By using platinum(II) chloride as a Lewis acid catalyst, concise and efficient syntheses of indole carbamates, 1,2-dihydroisoquinoline carbamates, macrocyclic indole carbamates, indole ureas, and indole phosphoranes have been achieved via tandem Hofmann-t
Gold(I)-catalyzed intramolecular hydroamination of unactivated C=C bonds with alkyl ammonium salts
Bender, Christopher F.,Widenhoefer, Ross A.
supporting information; experimental part, p. 2741 - 2743 (2009/02/04)
A mixture of (5)AuCl {5 = PCy2[2-(2,6-C6H 3(OMe)2)C6H4]} and AgOTf catalyzes the intramolecular hydroamination of unactivated C=C bonds with primary and secondary ammonium salts. The Royal
Heteroatom-Directed Metalation. Lithiation of N-Propenylbenzamides and N-Propenyl-o-toluamides. Novel Routes to Ortho-Substituted Primary Benzamide Derivatives and N-Unsubstituted Isoquinolin-1(2H)-ones
Fisher, Lawrence E.,Muchowski, Joseph M.,Clark, Robin D.
, p. 2700 - 2705 (2007/10/02)
Reaction of N-propenylbenzamides 4 and 9, obtained by LDA-induced isomerization of the corresponding N-allylbenzamides, 1, 8, and 14, with 2 equiv of sec-butyllithium or tert-butyllithium at low temperature regiospecifically generates the highly reactive N,ortho-dilithiated species (e.g., 5 and 17).These dilithio species react avidly with a wide spectrum of electophilic reagents, including alky halides, giving adducts which on hydrolysis with warm 50percent aqueous acetic acid are converted into ortho-substituted primary benzamides in excellent yields.Ortho-lithiation of N-propenylbenzamides is thus formally equivalent to ortho-lithiation of primary benzamides themselves.The utility of this important, previously unknown, synthetic operation is enhanced by the well-known facility with which the primary amide moiety can be transformed into other useful functional groups, as exemplified by the synthesis of 2-methoxy-6-methylbenzoic acid (12) and 2-methoxy-6-methylbenzonitrile (13) from N-propenyl-2-methoxybenzamide (9).N-Propenyl-o-toluamide (7) undergoes regiospecific dilithiation on nitrogen and on the methyl group under conditions analogous to those used for the N-propenylbenzamides.These dilithio species react with DMF or "Weinreb type" amides to give condensation products which cyclize to N-propenylisoquinolin-1(2H)-ones under mildly acidic conditions.Removal of the N-propenyl moiety under more strongly acidic conditions provides N-unsubstituted isoquinolin-1(2H)-ones with high overall efficiency.This process is exemplified by the synthesis of isoquinolin-1(2H)-one (23) and its 3-n-butyl congener 26 from N-propenyl-2-methylbenzamide (7).
