Synthesis of Alkaloid Sinomenine Derivatives Containing a Pyrimidine Substituent in Ring A

Autor:	Victor Kartsev, Anastasiya O. Finke, Elvira E. Shults
Rok vydání:	2021
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Ketone Phenylacetylene chemistry Pyrimidine Organic Chemistry Substituent Molecule Ring (chemistry) Medicinal chemistry Catalysis Benzoic acid
Zdroj:	Chemistry of Heterocyclic Compounds. 57:934-943
ISSN:	1573-8353 0009-3122
DOI:	10.1007/s10593-021-03003-4
Popis:	The alkaloid 4-O-methylsinomenine was modified by introducing pyrimidine substituents at the C-1 position of the backbone. Two methods were used to synthesize these hybrid molecules. The first method involves the preparation of 1-ethynyl-4-O-methylsinomenine and a sequence of cross-coupling reactions with benzoic acid chlorides and cyclocondensation with amidines. The second method is based on palladium-catalyzed carbonylation–cross coupling of 1-iodo-4-O-methylsinomenine with phenylacetylene in the presence of Mo(CO)6 as a source of CO in MeCN and subsequent cyclocondensation of alkynyl ketone with amidines. The carbonylation–crosscoupling reaction proceeded selectively in the presence of the PdCl2/(1-Ad)2PBn catalytic system.
Databáze:	OpenAIRE
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