Synthesis of antiviral tetrahydrocarbazole derivatives by photochemical and acid-catalyzed C-H functionalization via intermediate peroxides (CHIPS).
نویسندگان
چکیده
The direct functionalization of C-H bonds is an important and long standing goal in organic chemistry. Such transformations can be very powerful in order to streamline synthesis by saving steps, time and material compared to conventional methods that require the introduction and removal of activating or directing groups. Therefore, the functionalization of C-H bonds is also attractive for green chemistry. Under oxidative conditions, two C-H bonds or one C-H and one heteroatom-H bond can be transformed to C-C and C-heteroatom bonds, respectively. Often these oxidative coupling reactions require synthetic oxidants, expensive catalysts or high temperatures. Here, we describe a two-step procedure to functionalize indole derivatives, more specifically tetrahydrocarbazoles, by C-H amination using only elemental oxygen as oxidant. The reaction uses the principle of C-H functionalization via Intermediate PeroxideS (CHIPS). In the first step, a hydroperoxide is generated oxidatively using visible light, a photosensitizer and elemental oxygen. In the second step, the N-nucleophile, an aniline, is introduced by Brønsted-acid catalyzed activation of the hydroperoxide leaving group. The products of the first and second step often precipitate and can be conveniently filtered off. The synthesis of a biologically active compound is shown.
منابع مشابه
The green synthesis of pyrano[3,2-c]quinoline-2,5-dione derivatives catalyzed by acidic ionic liquid under ultrasound irradiation
Abstract-A novel and efficient method has been developed for the synthesis of pyrano[3,2-c]quinoline-2,5-dione derivatives by the convenient ultrasound-mediated condensation of 4-hydroxyquinolin-2-one with Meldrum’s acid and aldehydes in the presence of a catalytic amount of [HMIm]HSO4 as a green, efficient and reusable acidic ionic liquid medium. The stability of the ionic liquid during the re...
متن کاملOne Pot Synthesis of Polyhydroquinolines Catalyzed by Sulfonic Acid Functionalized SBA-15 as a New Nanoporous Acid Catalyst under Solvent Free Conditions
Sulfonic acid functionalized SBA-15 (SBA-Pr-SO3H) as a new nanoporous acid catalyst was used in the one-pot synthesis of polyhydroquinolines derivatives via the Hantzsch four component condensation reaction of aldehydes, b-ketoesters, dimedone and ammonium acetate under solvent free conditions with short reaction time in excellent yields. SBA-P...
متن کاملAn efficient synthesis of 4-aryl-7-benzylidene-hexahydro-2H-cyclopenta[d] pyrimidin-2-ones/thiones catalyzed by p-dodecylbenzenesulfonic acid
A new and efficient method has been developed for the synthesis of 4-aryl-7-benzylidene-1,3,4,5,6,7-hexahydro-2H-cyclopenta[d]pyrimidin-2-ones through Biginelli-like reaction of cyclopentanone, with urea/thiourea and aromatic aldehyde employing p-dodecylbenzenesulfonic acid (DBSA) as a recyclable catalyst under solvent-free condition. The recovered catalyst was recycled for further runs. The pr...
متن کاملA green, efficient, and rapid procedure for the synthesis of pyrano[3,2-c] quinoline and pyrano[3,2-c]pyridone derivatives catalyzed by [BMIm]Cl
A highly practical and efficient preparation of pyrano[3,2-c]pyridone and pyrano[3,2-c]quinoline derivatives was developed via an ionic liquid mediated and promoted multi-component reaction of malononitrile, aldehyde, and 4-hydroxyquinolin-2(1H)-one or 4-hydroxy-6-methylpyridin-2(1H)-one. The combinatorial syntheses were achieved for the first time without applying extra activation energy at am...
متن کاملA green, efficient, and rapid procedure for the synthesis of pyrano[3,2-c] quinoline and pyrano[3,2-c]pyridone derivatives catalyzed by [BMIm]Cl
A highly practical and efficient preparation of pyrano[3,2-c]pyridone and pyrano[3,2-c]quinoline derivatives was developed via an ionic liquid mediated and promoted multi-component reaction of malononitrile, aldehyde, and 4-hydroxyquinolin-2(1H)-one or 4-hydroxy-6-methylpyridin-2(1H)-one. The combinatorial syntheses were achieved for the first time without applying extra activation energy at am...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Journal of visualized experiments : JoVE
دوره 88 شماره
صفحات -
تاریخ انتشار 2014