American Chemical Society
Browse
jo7b00947_si_002.pdf (3.68 MB)

Regio- and Diastereoselective Synthesis of Dihydropyridopyrimidines via Cascade Reactions of 2‑Aminopyridines with Morita–Baylis–Hillman Bromides of Nitroalkenes

Download (3.68 MB)
journal contribution
posted on 2017-05-24, 00:00 authored by Lakshminarayana Satham, Irishi N. N. Namboothiri
The Morita–Baylis–Hillman (MBH) bromides of nitroalkenes have been employed as bielectrophiles for the first time. The 1,3-bielectrophilic reactivity of the MBH bromides has been demonstrated in the synthesis of 3,4-dihydro-2H-pyrido­[1,2-a]­pyrimidines. The reaction of MBH bromides with 2-aminopyridines takes place in the absence of any reagent in a cascade SN2′-6-endo-trig fashion and is completely regioselective and highly stereoselective. The products, in their hydrobromide salt form, could be conveniently isolated and purified by crystallization. The high stereoselectivity has been rationalized in terms of the greater stability of the transition state in which the Ar and NO2 groups are anti to each other.

History

Usage metrics

    The Journal of Organic Chemistry

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC