74371-91-8Relevant academic research and scientific papers
Heteroannulation of arynes with N-aryl-α-aminoketones for the synthesis of unsymmetrical N-aryl-2,3-disubstituted indoles: An aryne twist of Bischler-Moehlau indole synthesis
Bunescu, Ala,Piemontesi, Cyril,Wang, Qian,Zhu, Jieping
, p. 10284 - 10286 (2013/10/22)
Reaction of 2-(trimethylsilyl)aryl triflates 1 with N-aryl-α-amino ketones 2 afforded N-aryl-2,3-disubstituted indoles in good to excellent yields with complete control of the substitution patterns. This methodology allowed for the first time a one-step s
Alternative reaction pathways in domino reactions of hydrazinediidozirconium complexes with alkynes
Gehrmann, Thorsten,Scholl, Solveig A.,Fillol, Julio Lloret,Wadepohl, Hubert,Gade, Lutz H.
supporting information; experimental part, p. 3925 - 3941 (2012/05/20)
Reaction of [Zr{(NAr)2Npy}(NMe2) 2] (Ar=3,5-xylyl: 2 a, mesityl: 2 b) with one or two molar equivalents of 1,1-diphenylhydrazine gave the mixed amido/hydrazido(1-) complex [Zr{(NMes)2Npy}(HNNPh2)(NMe2)] (3), the bis-hydrazido complex [Zr{(NMes)2Npy}(HNNPh 2)2] (4), and, in the presence of excess 4-dimethylaminopyridine (DMAP), hexacoordinate hydrazinediidozirconium complexes [Zr{(NXyl)2Npy}(=NN(Me)Ph)(dmap)2] (5) and [Zr{(NXyl)2Npy}(=NNPh2)(dmap)2] (6). The reaction of one equivalent of the zirconium-hydrazinediide [Zr{(NTBS) 2Npy}(NNPh2)(py)] (1) with disubstituted alkynes at RT for 16 h led to the formation of seven-membered diazazirconacycles 7 a-7 e in high yields. Similar reactivity was observed by reacting bis-amido complex 2 b with one molar equivalent of the corresponding alkyne and diphenylhydrazine. The formation of the seven-membered zirconacycles implied a key coupling step that involved the alkyne and one of the aryl rings of the diphenylhydrazinediido ligand. In some cases, such as the reaction with 2-butyne, the corresponding metallacycle was only obtained in modest yields (45 % for the reaction with 2-butyne) and a second major product, vinylimido complex 9, was formed in almost equal amounts (42 %) by 1,2-amination (formal insertion of the alkyne). The formation of compounds 7 a and 9 followed in part the same sequence of reaction steps and a key intermediate, an azirinido complex, represented a "bifurcation point" in the reaction network. Reaction of 1.2 equivalents of several diarylhydrazines and various substituted alkynes (1 equiv) at ambient temperature (or at 80 °C) in the presence of 10 mol % [Zr{(NXyl)2Npy}(NMe2)2] (2 a) gave the corresponding indole derivatives. On the other hand, the replacement of 1,1-diarylhydrazines by 1-methyl-1-phenyl hydrazine led to head-to-head cis-1,3-enynes in good yields. A fork in the road: Azirinidozirconium species A is the key intermediate for two reaction pathways in the metal-catalyzed coupling of diarylhydrazines and alkynes. Electrophilic metal-azirinide attack at the ortho C atom (C) affords substituted indoles. Copyright
Zirconium-catalyzed multistep reaction of hydrazines with alkynes: A non-fischer-type pathway to indoles
Gehrmann, Thorsten,Lloret Fillol, Julio,Scholl, Solveig A.,Wadepohl, Hubert,Gade, Lutz H.
supporting information; experimental part, p. 5757 - 5761 (2011/08/05)
Dominos at zirconium: A cascade of N-N and C-H scissions and C-C and C-N coupling steps in the coordination sphere of zirconium directly converts alkynes and hydrazines into indoles. The reaction pathway differs fundamentally from that of the Fischer indo
Efficient synthesis of indoles using [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines
Miyata, Okiko,Takeda, Norihiko,Kimura, Yasuo,Takemoto, Yoshiji,Tohnai, Norimitsu,Miyata, Mikiji,Naito, Takeaki
, p. 3629 - 3647 (2007/10/03)
[3,3]-Sigmatropic rearrangement of N-trifluoroacetyl enehydrazines provides a novel method for the construction of indoles. N-Trifluoroacetyl enehydrazine having a cyclopentene ring smoothly underwent [3,3]-sigmatropic rearrangement followed by cyclizatio
Thermal cyclization of N-trifluoroacetyl enehydrazines under mild conditions: A novel entry into the Fischer indole synthesis
Miyata, Okiko,Kimura, Yasuo,Muroya, Kanami,Hiramatsu, Hajime,Naito, Takeaki
, p. 3601 - 3604 (2007/10/03)
An efficient thermal cyclization of N-trifluoroacetyl enehydrazines for the synthesis of indoles is described.
Rearrangement of 1-Arylindoles to 5H-Dibenzazepines
Tokmakov, Gennadii P.,Grandberg, Igor I.
, p. 2091 - 2098 (2007/10/02)
An unusual acid-catalyzed rearrangement of 1-arylindoles 1 to 5H-dibenzazepines 2 has been discovered.It can be used for the preparation of 2.The influence of the nature and the position of the substituents in the initial molecule 1 on the rearrangement is discussed.A possible mechanism of the reaction is suggested.A convenient method for preparation of 1-arylindoles 1c-k by means of arylation of 1-unsubstituted indoles with aryl halides by the Ullmann reaction is described.
N-Phenylindoline derivatives, and pharmaceutical compositions containing them
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, (2008/06/13)
2-aminoethyl-1-phenylindolines are useful as anti-diabetic and anti-obesity agents.
