38118-69-3Relevant academic research and scientific papers
Aqueous copper nitrate catalyzed synthesis of 3-alkylideneoxindoles from α-diazo-ketoanilides
Mo, Shanyan,Yang, Zhanhui,Xu, Jiaxi
, p. 3923 - 3929 (2014/06/24)
An economical, practical, and green protocol with which to synthesize 3-alkylideneoxindoles from α-diazo-ketoanilides has been developed. The approach employs inexpensive Cu(NO3)2·3H 2O as catalyst and environmentally friendly water as solvent, and achieves moderate to excellent yields. The method has good tolerance to a range of N-alkyl and N-aryl groups, including electron-withdrawing and electron-donating groups on the aromatic ring, ortho-, meta-, and para-substituents, and -aliphatic and -aromatic keto groups. A plausible mechanism involving intramolecular aromatic metal carbene electrophilic addition as the key step is proposed. Inexpensive Cu(NO3)2· 3H2O catalyst and environmentally friendly water solvent are employed for the transformation of α-diazo-ketoanilides into 3-alkylidene- oxindoles. The process is easily handled, economical, environmentally friendly, and can be used to convert a broad range of substrates in moderate to excellent yields. An intramolecular aromatic metal carbene electrophilic addition mechanism is proposed. Copyright
Ruthenium-catalyzed intramolecular cyclization of diazo-β-ketoanilides for the synthesis of 3-alkylideneoxindoles
Chan, Wai-Wing,Kwong, Tsz-Lung,Yu, Wing-Yiu
experimental part, p. 3749 - 3755 (2012/06/01)
With [Ru(p-cymene)Cl2]2 as catalyst, diazo-β-ketoanilides would undergo intramolecular carbenoid arene C-H bond functionalization to afford 3-alkylideneoxindoles in up to 92% yields. The reaction occurs under mild conditions and exhibits excellent chemoselectivity. The lack of primary KIE (kH/kD ～ 1) suggests that the reaction should not proceed by rate-limiting C-H bond cleavage; a mechanism involving cyclopropanation of the arene is proposed.
Intramolecular hydrogen bonding-assisted cyclocondensation of α-diazoketones with various amines: A strategy for highly efficient Wolff 1,2,3-triazole synthesis
Wang, Zikun,Bi, Xihe,Liao, Peiqiu,Zhang, Rui,Liang, Yongjiu,Dong, Dewen
supporting information; experimental part, p. 7076 - 7078 (2012/08/14)
A catalytic and highly efficient Wolff's cyclocondensation of α-diazoketones with aromatic and aliphatic amines has been realized for the first time by utilizing the strategy of an intramolecular hydrogen bonding-activating carbonyl group. This approach successfully solved the challenging problem of poor condensation efficiency in Wolff 1,2,3-triazole synthesis, and constitutes a powerful method for the synthesis of highly functionalized 1,2,3-triazoles. The Royal Society of Chemistry 2012.
Synthesis of 3-alkoxy/aryloxy - Lactams using diazoacetate esters as ketene precursors under photoirradiation
Qi, Hengzhen,Yang, Zhanhui,Xu, Jiaxi
experimental part, p. 723 - 730 (2011/04/24)
3-Alkoxy/aryloxy - lactams are synthesized in satisfactory to good yields from the reaction of imines and alkyl/aryl di-azoacetates under photoirradiation conditions. Typically, trans - lactams are obtained as the major products from linear imines using the current method. By contrast, the corresponding thermal reaction of imines and alkoxy/aryloxyacetyl chlorides, or their equivalents, in the presence of triethylamine affords cis - lactams as the major or exclusive products. The formation of trans - lactams from linear imines is attributed to isomerization of the imines from their trans-isomers into syn-isomers under UV irradiation. The reported method represents a metal-free and neutral approach for the synthesis of 3-alkoxy/aryloxy - lactams. Georg Thieme Verlag Stuttgart New York.
Rhodium(II) Acetate and Nafion-H Catalyzed Decomposition of N-Aryldiazoamides. An Efficient Synthesis of 2(3H)-Indolinones
Doyle, Michael P.,Shanklin, Michael S.,Pho, Hoan Q.,Mahapatro, Surendra N.
, p. 1017 - 1022 (2007/10/02)
N-Aryldiazoamides undergo facile intramolecular aromatic substitution to form 2(3H)-indolinones in high yield when these reactions are performed in the presence of a catalytic amount of rhodium(II) acetate.Diazoacetamides react smoothly at room temperature in dichloromethane, whereas the corresponding less reactive diazoacetoacetamides respond in the refluxing benzene.A meta methoxy substituent directs substitution solely to its para position, but a meta methyl substituent offers virtually no selectivity for substitution.N-α-Naphtyldiazoacetamide undergoes exclusive intr amolecular substitution at the β-position.The perfluororesinsulfonic acid Nafion-H also catalyzes the decomposition of N-aryldiazoacetamides, but not N-aryldiazoacetamides, and yields of 2-idolinones are even greater than those obtained with rhodium carboxylate catalysis even though higher reaction temperatures are required to initiate decomposition
