Addition of malonic esters to azoalkenes generated in situ from α-bromo- and α-chlorohydrazones

Addition of malonic esters to azoalkenes generated in situ from α-bromo- and α-chlorohydrazones Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2021, Volume: 83, Article number : 153414, Pages count : DOI: 10.1016/j.tetlet.2021.153414

Authors

Kokuev Aleksandr O. ^1,2 , Ioffe Sema L. ² , Sukhorukov Alexey Yu. ²

Affiliations

1	D. Mendeleev University of Chemical Technology of Russia, Miusskaya sq., 9, Moscow 125047, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect, 47, Moscow 119991, Russian Federation

Michael addition of malonic esters to azoalkenes generated in situ from α-bromo- and α-chlorohydrazones was accomplished. Both aliphatic and aromatic substrates bearing different functional groups are tolerated. The use of a strong base (sodium hydride) for generation of azoalkenes and deprotonation of malonate was found to be essential for a successful coupling. Synthetic potential of the obtained β-hydrazonoalkylmalonates was demonstrated by their smooth conversion into five- and six-membered N-heterocycles, functionalized hydrazides, 2-(2-oxo-2-arylethyl)malonates and 2-arylethylmalonates.

Kokuev A.O. , Ioffe S.L. , Sukhorukov A.Y.
Addition of malonic esters to azoalkenes generated in situ from α-bromo- and α-chlorohydrazones
Tetrahedron Letters. 2021. V.83. 153414 . DOI: 10.1016/j.tetlet.2021.153414 WOS Scopus OpenAlex

Web of science:	WOS:000738831700010
Scopus:	2-s2.0-85115949470
OpenAlex:	W3201565322

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OpenAlex	3
Scopus	3
Web of science	3