One-pot total synthesis of streptindole, arsindoline B and their congeners through tandem decarboxylative deaminative dual-coupling reaction of amino acids with indoles.
نویسندگان
چکیده
This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM scaffolds and its further application to the one-pot total synthesis of natural products. This method featured a stimulating example of activating amino acids in one pot as multi-carbon building blocks for transformation into final targets which are equipped with amino acid side chain backbones.
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 کاملPd-catalyzed decarboxylative coupling of propiolic acids: one-pot synthesis of 1,4-disubstituted 1,3-diynes via Sonogashira-homocoupling sequence.
One-pot synthesis of symmetric 1,4-disubstituted 1,3-diynes from iodoarenes and propiolic acid via Sonogashira reaction followed by Pd-catalyzed decarboxylative homocoupling is developed in high yields. Also, this system allows the one-pot synthesis of unsymmetric 1,4-disubstituted 1,3-diynes by cross-coupling of two different 3-substituted propiolic acids.
متن کاملOne-pot, organocatalytic synthesis of spirooxindoles using citric acid in aqueous media
Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications.The development of multicomponent reactions designed to produce elaborate biologically active compounds has become an important area of research in organic, combinatorial, and medicinal chemistry. in this Manuscript, a facile and efficient multicomponent synthesis of functional...
متن کاملSynthesis of bis(indolyl)methanes Catalyzed by Triethylborane
Triethylborane (TEB) was found to be a mild, efficient, and acid catalyst in electrophilic substitution reaction of indoles with aldehydes compounds to afford the corresponding bis(indolyl)methanes. Vibrindole A (5) and bis(indolyl)methanes derivatives 16 and 18 were synthesized using this methodology. Compound 16 is an intermediary in the synthesis of the natural bisindoles arsindoline B (2) a...
متن کاملCopper-catalyzed ring expansion of 2-aminobenzothiazoles with alkynyl carboxylic acids to 1,4-benzothiazines.
A new ring expansion of 2-aminobenzothiazoles with alkynyl carboxylic acids was developed, which allows for one-pot synthesis of 1,4-benzothiazines in moderate to excellent yields. The cascade reaction was achieved through decarboxylative coupling, nucleophilic ring-opening reaction and intramolecular hydroamination process.
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:
- Organic & biomolecular chemistry
دوره 13 14 شماره
صفحات -
تاریخ انتشار 2015