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Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines
Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines
- Source :
- Angewandte Chemie (International ed. in English). 56(15)
- Publication Year :
- 2017
-
Abstract
- Amidine is a notable nitrogen-containing structural motif found in bioactive natural products and pharmaceuticals. Herein, a novel rhodium(I)-catalyzed tandem reaction of readily accessible azides with isonitriles and boronic acids via a carbodiimide intermediate is achieved. This protocol offers an alternative approach toward N-sulfonyl-, N-acyl-, and N- phosphoryl-functionalized, as well as general N-aryl and N-alkyl amidines with broad substrate scope. In addition, functionalized guanidines can also been synthesized when amines are used instead. The accomplishment of estrone-derived amidine and glibenclamide bioisosteres further reveals the practical utility of this strategy.
- Subjects :
- Tandem
010405 organic chemistry
Substrate (chemistry)
chemistry.chemical_element
General Chemistry
General Medicine
010402 general chemistry
Combinatorial chemistry
01 natural sciences
Catalysis
Rhodium
0104 chemical sciences
Amidine
chemistry.chemical_compound
chemistry
Cascade reaction
Organic chemistry
Azide
Boronic acid
Carbodiimide
Subjects
Details
- ISSN :
- 15213773
- Volume :
- 56
- Issue :
- 15
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie (International ed. in English)
- Accession number :
- edsair.doi.dedup.....94e0e75b87e4a01f8b30d81ff8b88d0f