One-pot formal [3+3] cycloaddition of isocyanoacetates with in situ-derived azoalkenes for the synthesis of 1, 4-dihydropyrimidine derivatives. (21st May 2021)

• Record Type: Journal Article
• Authors: Liu, Qiang; Chen, Jia-Hui; Yao, Min; Zhao, Zhuo-Yu; Liu, Xiang-Yi; Zhao, Xiao-Li; Shi, Min; Zhao, Mei-Xin
• Is Part Of: Tetrahedron. Volume 88(2021)
• Publication Date: 2021-05-21
• Subjects: Isocyanoacetates -- Azoalkenes -- Conjugate addition -- Formal [3+3] cycloaddition -- Heterocycles; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.132122
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The first conjugate addition of α-isocyanoacetates with in situ generated azoalkenes from α-halogeno hydrazones in the presence of Cs2 CO3 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. Graphical abstract: Image 1