Lewis-acid catalyzed N-acyliminium ion cyclodimerization: synthesis of symmetrical 1,4-dioxanes

Author(s)

Ali, Bakhat ^[1] ; Zukerman-Schpector, Julio ^[2] ; Ferreira, Fernando P. ^[3] ; Shamim, Anwar ^[4] ; Pimenta, Daniel C. ^[5] ; Stefani, Helici A. ^{[1, 4]}

Affiliation

^[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo, SP - Brazil

^[2] Univ Fed Sao Carlos, Dept Quim, BR-13560 Sao Carlos, SP - Brazil

^[3] Univ Fed Sao Paulo, Dept Biofis, Sao Paulo, SP - Brazil

^[4] Univ Sao Paulo, Inst Quim, Sao Paulo, SP - Brazil

^[5] Inst Butantan, Sao Paulo, SP - Brazil

• Document type: Journal article
• Source: Tetrahedron Letters; v. 56, n. 9, p. 1153-1158, FEB 25 2015.
• Web of Science Citations: 4

Abstract

The cyclodimerization reaction of N-substituted-5-hydroxy-pyrrolydinones promoted by BF3 center dot Et2O and HCl to obtain symmetrical 1,4-dioxane derivatives was achieved in moderate to good yields, mild conditions, and short reaction times. These transformations render a promising alternative route that provides access to diverse 1,4-dioxane derivatives with a wide structural diversity. (C) 2015 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 12/00424-2 - Synthesis of small libraries using potassium Organotrifluoroborates in Suzuki-Miyaura reactions
• Grantee: Helio Alexandre Stefani
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 12/17954-4 - Cyclization reaction of Acetyl- and Ethylpyrrolidin-2-one with Potassium Organotrifluoroborate Salts
• Grantee: Bakhat Ali
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 11/11499-0 - Bioisosterism in the design of new antichagasic agents: integration of computational and experimental strategies
• Grantee: Gustavo Henrique Goulart Trossini
• Support Opportunities: Regular Research Grants