93007-96-6Relevant academic research and scientific papers
Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor
Abdelli, Abderrahmen,Efrit, Mohamed Lotfi,El-Marrouki, Dalel,Gros, Philippe C.,M’Rabet, Hédi,Touchet, Sabrina
, p. 1722 - 1731 (2021/06/25)
A convergent strategy is reported for the construction of nitrogen-containing heterocycles from common substrates: 1,4-diketones and primary amines. Indeed, by just varying the substrates, the substituents, or the heating mode, it is possible to selectively synthesize indole, indolone (1,5,6,7-tetrahydroindol-4-one), or cinnoline (5,6,7,8-tetrahydrocinnoline) derivatives in moderate to excellent yields.
Iron-catalyzed synthesis of polysubstituted pyrroles via [4C+1N] cyclization of 4-acetylenic ketones with primary amines
Wang, Yeming,Bi, Xihe,Li, Dehua,Liao, Peiqiu,Wang, Yidong,Yang, Jin,Zhang, Qian,Liu, Qun
scheme or table, p. 809 - 811 (2011/04/15)
A highly efficient iron-catalyzed approach to polysubstituted pyrroles has been developed through the [4C+1N] cyclization of 4-acetylenic ketones with primary amines, leading to the synthesis of a variety of tetra- and fully-substituted pyrroles as well a
Pyrrolo[2,3-h]quinolinones: Synthesis and photochemotherapic activity
Barraja, Paola,Diana, Patrizia,Lauria, Antonino,Montalbano, Alessandra,Almerico, Anna Maria,Dattolo, Gaetano,Cirrincione, Girolamo,Viola, Giampietro,Dall'Acqua, Francesco
, p. 2809 - 2811 (2007/10/03)
A series of derivatives of the new ring system pyrrolo[2,3-h]quinoline-2-one was synthesized and evaluated as photoreagents toward cultured human tumor cells. Remarkable phototoxycity resulted for some derivatives, especially those bearing the phenyl grou
New approach for the general synthesis of oxotetrahydroindoles via intramolecular cycloadditions of azomethine ylides with tethered alkynes
Nayyar, Naresh K.,Hutchison, Darrell R.,Martinelli, Michael J.
, p. 982 - 991 (2007/10/03)
A new method for the synthesis of oxotetrahydroindoles has been achieved employing an intramolecular dipolar cycloaddition approach involving mesoionic species (munchnones) with electron-deficient alkynes. The methodology is quite general and convergent as shown by the synthesis of a variety of tri- and tetrasubstituted oxotetrahydroindoles 18, 21, 24, 27, 30, and 34. LiI-based ester cleavage in the presence of an electrophilic acetylenic ketone was critical for formation of the requisite cycloaddition substrates. The cycloaddition is virtually unaffected by the presence of gem-dimethyl groups in the side chain (cf. 38). The presence of a substituted benzyl or a phenethyl moiety on nitrogen, a polarized acetylene, and an appropriate tether between dipole and dipolarophile are essential for obtaining optimal efficiency.
A simple and general synthesis of 4-oxo-4,5,6,7-tetrahydroindoles via a novel intramolecular 1,3-dipolar cycloaddition approach
Hutchison, Darrell R.,Nayyar, Naresh K.,Martinelli, Michael J.
, p. 2887 - 2890 (2007/10/03)
A general synthesis of 4-keto-4,5,6,7-tetrahydroindoles 6-12 has been achieved in two steps using a new intramolecular 1,3-dipolar cycloaddition approach in moderate yields (45-60%). The potential of this methodology is demonstrated by the synthesis of a mitomycin skeleton (15) and a topoisomerase-1 inhibitor skeleton (17).
