Simple Syntheses of 3-Substituted Indoles and their Application for High Yield 14C-Labelling

نویسندگان

  • Jürgen Schallenberg
  • Eckart Meyer
چکیده

3-Substituted Indoles, Indole Alkaloids, UV Spectra, MS Spectra, 1H NMR spectra Methods are described which allow the synthesis of several plant indole alkaloids and their metabolites at different scales. Compounds synthesized include gramine (1) (3-dimethylaminomethylindole) which is directly derived from indole, while its biosynthetic precursors 3-aminomethylindole (3) and 3-methylaminomethylindole (2) as well as indole3-carboxylic acid (7) are synthesized via indole-3-aldehyde (6). Slight changes of the experimental conditions allow syntheses with high yields not only at the molar but also at the /imolar level. This is extremely useful when isotope labelled compounds of high specific radioactivity are required for studies of plant metabolism.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

[BMIm]HSO4 as a Green and Highly Efficient Catalyst for One-pot Synthesis of 3-Substituted Indoles under Ultrasound Irradiation

A practical and green synthesis of 3-substituted indoles is reported via three-component coupling reaction of indoles, aldehydes and N-methylaniline in the presence of the acidic ionic liquid 1-butyl-3-methylimidazolium hydrogen sulfate ([BMIm]HSO4) under ultrasound irradiation at room temperature. The significant features of this procedure are high yields of the products, simple work-up, opera...

متن کامل

Syntheses of Substituted 1,3,4-Oxadiazole, 1,3,4-Thiadiazole and 1,2,4-Triazole Derivatives as Potential Antimicrobial Agents

A series of 2-(4-nitro-1-imidazolylmethyl)-1,3,4-oxadiazole, 1,3,4-triazole and 3-(4-nitro-1-imidazolylmethyl)-1,2,4-triazole derivatives were synthesized and tested for their antimicrobial activity. Some of the tested compounds were active against Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, Clostridium difficile, Aspergillus niger and Cryptococcus neoformans.

متن کامل

Nano silica sulfuric acid catalyzed synthesis of 2-substituted aryl (indolyl) kojic acid derivatives

Nano silica sulfuric acid as a solid acid, was described to be an effective catalyst for one-pot three-component reaction of kojic acid, aryl aldehydes and indoles for the preparation of 2-substituted aryl (indolyl) kojic acid derivatives. The catalyst was prepared by combination of chlorosulfonic acid to nano silica gel. The size of nanoparticles were observed with SEM.All prepared compounds w...

متن کامل

Nano silica sulfuric acid catalyzed synthesis of 2-substituted aryl (indolyl) kojic acid derivatives

Nano silica sulfuric acid as a solid acid, was described to be an effective catalyst for one-pot three-component reaction of kojic acid, aryl aldehydes and indoles for the preparation of 2-substituted aryl (indolyl) kojic acid derivatives. The catalyst was prepared by combination of chlorosulfonic acid to nano silica gel. The size of nanoparticles were observed with SEM.All prepared compounds w...

متن کامل

Pharmacological properties of some 3-substituted indole derivatives, a concise overview

Indole is a nitrogen-containing heterocycle. It is a very important motif in agriculture and pharmacy. Many compounds containing indole moiety has been isolated form nature. It is also an important part in natural alkaloids. Tryptophan is an amino acid which posses indole. 3-Sustituted indoles are the main group of its derivatives. Because the wide-spread application of 3-substituted indolic co...

متن کامل

ذخیره 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 نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2012