Jump to main content
Jump to site search

Issue 2, 2015
Previous Article Next Article

Synthesis of five- and six-membered heterocycles by dimethyl carbonate with catalytic amounts of nitrogen bicyclic bases

Author affiliations

Abstract

A catalytic amount of a nitrogen bicyclic base, i.e., DABCO, DBU or TBD, is effective for the one-pot synthesis of heterocycles from 1,4-, 1,5-diols and 1,4-bifunctional compounds via dimethyl carbonate chemistry under neat conditions. Nitrogen bicyclic bases that were previously shown to have enhanced the reactivity of DMC in methoxycarbonylation reaction by a BAc2 mechanism are herein used for the first time as efficient catalysts for cyclization reactions encompassing both BAc2 and BAl2 pathways. This synthesis procedure was also applied to a large scale synthesis of cyclic sugars, isosorbide and isomannide, starting from D-sorbitol and D-mannitol, respectively. The resulting anhydro sugar alcohols were obtained as pure crystalline compounds that did not require any further purification or crystallization.

Graphical abstract: Synthesis of five- and six-membered heterocycles by dimethyl carbonate with catalytic amounts of nitrogen bicyclic bases

Back to tab navigation

Supplementary files

Publication details

The article was received on 19 Sep 2014, accepted on 07 Nov 2014 and first published on 11 Nov 2014


Article type: Paper
DOI: 10.1039/C4GC01822B
Citation: Green Chem., 2015,17, 1176-1185
  •   Request permissions

    Synthesis of five- and six-membered heterocycles by dimethyl carbonate with catalytic amounts of nitrogen bicyclic bases

    F. Aricò, S. Evaristo and P. Tundo, Green Chem., 2015, 17, 1176
    DOI: 10.1039/C4GC01822B

Search articles by author

Spotlight

Advertisements