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One-pot formal [3+3] cycloaddition of isocyanoacetates with in situ-derived azoalkenes for the synthesis of 1,4-dihydropyrimidine derivatives.
- Source :
-
Tetrahedron . May2021, Vol. 88, pN.PAG-N.PAG. 1p. - Publication Year :
- 2021
-
Abstract
- The first conjugate addition of α-isocyanoacetates with in situ generated azoalkenes from α-halogeno hydrazones in the presence of Cs 2 CO 3 has been developed. The reaction condition was suitable to various α-aryl substituted isocyanoacetates as well as aryl and alkyl-substituted α-halogeno hydrazones, affording the corresponding products in good to high yields. The adducts can be easily transformed into biologically attractive 1,4-dihydropyrimidine derivatives via an intramolecular cyclization by treating with AgOAc. The one-pot conjugate addition/intramolecular cyclization has also been investigated to furnish the formal [3 + 3] cycloadduct, 1,4-dihydropyrimidine derivatives. [Display omitted] [ABSTRACT FROM AUTHOR]
- Subjects :
- *RING formation (Chemistry)
*CARBON dioxide
*HYDRAZONES
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 88
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 150411086
- Full Text :
- https://doi.org/10.1016/j.tet.2021.132122