Studies on the Claisen rearrangements in the indolo[2,3-b]quinoline system.
نویسندگان
چکیده
A study of the effect of substrate structure on a Claisen-aza-Cope reaction is presented including a rationalisation of the reaction outcome using DFT calculations. An asymmetric version of the reaction is also described that is of relevance to a proposed approach to the communesin family of natural products.
منابع مشابه
The synthesis of indolo[2,3-b]quinoline derivatives with a guanidine group: highly selective cytotoxic agents.
The synthesis of indolo[2,3-b]quinoline derivatives containing guanidine, amino acid or guanylamino acid substituents as well as their in vitro evaluation for the cytotoxic and antifungal activity are reported. The influence of the guanidine group on the selective cytotoxic and hemolytic properties of indolo[2,3-b]quinoline was investigated. Most of the compounds displayed a high cytotoxic acti...
متن کاملKinetic and thermodynamic study of substituent effect on the Claisen rearrangement of para-substituted SI aryl ether: a Hammett study via DFT
In order to find the susceptibility of the Claisen rearrangement and next proton shift reaction of ally) aryl etherto the substiment effects in pan position, the kinetic and the:rmodynamie parameters are calculated at The33 LTP level using 6-3110. b asis set. The calculated activation energies for the rearrangements and protonshift reactions are around 3133 kcaUmol and 52.16 kcal/mol, nap.. liv...
متن کاملIodine mediated intramolecular C2-amidative cyclization of indoles: a facile access to indole fused tetracycles.
A novel and metal-free I2-mediated intramolecular C2 amidation of indoles under mild reaction conditions is developed. This methodology affords various indole fused tetracyclic compounds, such as benzo[4,5]imidazo[1,2-a]indoles by intramolecular C2 amidation of N-aryl substituted indoles. This C2 sulfonamidative cyclization also offers convenient access to indolo[2,3-b]indoles and dihydroindolo...
متن کاملPalladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines.
A series of indolo[2,3-b]quinoxaline derivatives were efficiently synthesized from 2,3-dibromoquinoxaline by two pathways. A one-pot approach using Pd-catalyzed two-fold C-N coupling and C-H activation reactions gave indolo[2,3-b]quinoxaline derivatives in good yields, but with limited substrate scope. In addition, a two-step approach to indolo[2,3-b]quinoxalines was developed which is based on...
متن کاملIndolo[2,3-b]quinoline Derivatives as Novel Promising Antitumor Agents
Chemistry Dept., Pharmaceutical Research Institute, Rydygiera St. 8, 01-793 Warszawa; Faculty of Biotechnology, Wrocław University, Fryderyk Joliot-Curie St. 14a, 50-383 Wrocław; Faculty of Chemistry, Wroclaw University of Technology, C.K. Norwid St.4/6, 50373 Wrocław; Experimental Acticancer Therapy Laboratory, Institute of Immunology and Experimental Therapy of Polish Academy of Sciences, Rud...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 8 2 شماره
صفحات -
تاریخ انتشار 2010