Solid-phase synthesis of 2,5-dihydro-1H-pyrroles, 1,3-dioxo-2,3,5,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazoles and 1,4-dioxo-1,2,3,4,6,8a-hexahydropyrrolo[1,2-a]pyrazines using a supported selenium resin.
A versatile combinatorial approach was developed for the rapid synthesis of 2,5-dihydro-1H-pyrroles, 1,3-dioxo-2,3,5,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazoles, and 1,4-dioxo-1,2,3,4,6,8a-hexahydropyrrolo[1,2-a]pyrazines libraries. The synthetic strategy includes electrophilic addition, dehydrohalogenation, 1,3-dipolar cycloaddition, N-acylation, amino carbonylation-cyclization, N-alkylation, lactamization, and oxidation-elimination.
Huang
Xian
X
Department of Chemistry, Zhejiang University, Hangzhou, PR China. huangx@mail.hz.zj.cn
Xu
Jian-Feng
JF
D000215:Acylation; D000478:Alkylation; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D003500:Cyclization; D054879:Halogenation; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012643:Selenium / Q000737:chemistry*
D007093:Imidazoles; D011719:Pyrazines; D011758:Pyrroles; D012643:Selenium