132923-50-3

Upstream product

• 5703-26-4 4-Methoxyphenylacetaldehyde 
• 19060-15-2 4-aminobutyraldehyde dimethyl acetal 
• 13472-81-6 3,5-dibromo-2-hydroxypyridine 
• 468066-76-4 3-[3,5-bis(4-methoxyphenyl)pyridin-2-yl]-2-propyn-1-ol 
• 468066-71-9 2-amino-3,5-bis(4-methoxyphenyl)pyridine 
• 468066-74-2 2-iodo-3,5-bis(4-methoxyphenyl)pyridine 
• 5720-07-0 4-methoxyphenylboronic acid 
• 35486-42-1 2-amino-3,5-dibromopyridine 
• 468066-77-5 3-[3,5-bis(4-methoxyphenyl)-pyridin-2-yl]propan-1-ol 

Relevant academic research and scientific papers

Syntheses of ficuseptine, juliprosine, and juliprosopine by biomimetic intramolecular chichibabin pyridine syntheses

(Chemical Equation Presented) Biomimetic intramolecular Chichibabin pyridine syntheses using two molecules of an aldehyde and 4-aminobutanal dimethyl acetal (6) proceed efficiently in AcOH at 95°C to give 2,3-dihydro-1H-indolizinium salts. Reaction occurs

Synthesis of Trisubstituted Pyridines via Chemoselective Suzuki–Miyaura Coupling of 3,5- and 4,6-Dibromo-2-tosyloxypyridines

Chemoselective Suzuki–Miyaura reactions on 3,5- and 4,6-dibromo-2-tosyloxypyridines have been studied for the preparation of trisubstituted pyridines. The optimized conditions allow for a facile access to 3,5- and 4,6-diaryl-2-tosyloxypyridines in yields of 8 to 99%. Further functionalization such as palladium-catalyzed amination and copper-free Sonogashira reaction of the tosylate group in the diarylpyridine derivatives obtained was accomplished for the synthesis of novel and biologically relevant trisubstituted pyridines. The formal synthesis of ficuseptine, a bioactive alkaloid, has also been achieved via the palladium-catalyzed cross-coupling reaction of 3,5-dibromo-2-tosyloxypyridine in 5 steps from 3,5-dibromo-2-hydroxypyridine with 50% overall yield. (Figure presented.).

Total synthesis of the indolizidinium alkaloid ficuseptine

The first total synthesis of ficuseptine [4,6-bis(4-methoxyphenyl)-1,2,3-trihydroindolizidinium chloride] (1), an alkaloid from Ficus septica, is described. The crucial steps in this five-step synthesis are a palladium-catalyzed bis(arylation) of a dibromopyridine under Suzuki conditions and a palladium-catalyzed alkynylation of an iodopyridine under Sonogashira conditions, as well as a novel Sandmeyer-type iodination of a 2-aminopyridine derivative. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.