Scribd Logo
Carica

Benvenuto in Scribd!

  • Heterocycles - PART 2 - Pall Knorr Pyrrole

    Caricato da

    Ghadeer M Hassan
    6 visualizzazioni4 pagine
    t5

    Copyright

    © © All Rights Reserved

    Formati disponibili

    PPTX, PDF o leggi online da Scribd

    Hai trovato utile questo documento?

    Questo contenuto è inappropriato?

    Segnala questo documento
    t5

    Copyright:

    © All Rights Reserved
    Scarica in formato PPTX, PDF o leggi online su Scribd
    Segnala contenuti inappropriati
    6 visualizzazioni4 pagine

    Heterocycles - PART 2 - Pall Knorr Pyrrole

    Caricato da

    Ghadeer M Hassan
    t5

    Copyright:

    © All Rights Reserved
    Scarica in formato PPTX, PDF o leggi online su Scribd
    Segnala contenuti inappropriati
    di 4
    Heterocycles from 1,4-diketones: the Paal-Knorr synthesis 2b When hexan-2,5-dione is treated with base an aldol-dehydration takes place, via the enolate, yielding an a,B-unsaturated ketone (3-methylcyclopentenone). Treatment with a strong acid however yields a furan (2,5-dimethylfuran) via the enol eo ® eee weeny 2 -H,0 -H20 oo Related reactions under acidic conditions can yield pyrroles and thiophenes. Hs, 4° Rt R20 ® < RNH2, H Rt Re —__» Mechanism of the Paal-Knorr synthesis 3a H ® we ex, mu we om ° vd Ss, proton \ transfer \ H3C’ 0 CH3 H3C" ‘CH H,0 © -H,0 H. conditions of thermodynamic control. The stable aromatic furan is ultimately produced. The reaction proceeds under oe Hse"Ng Hy HC CH3 © Paal-Knorr synthesis: pyrroles and thiophenes 3b The chemistry involved here is essentially the same as the furan example before, but an enamine or thioenol intermediate is needed XH © © ar) XH, wo yom eo H3C- oH wok Loi, 0 Oo 0 0 = = 0° n X=NR,X=S \ ON 7 proton transfer enamine (X=NR) or thioenol (X=S) H 4® XH : H,C: CH3 wo Lon, Oo Xx. 0 0® OM oH \ M22 Ok woX Sox, neh dom SF eA Hs > % HO 7® Paal-Knorr synthesi: : examples 4a Work out the products from the following reactions: HPO, NH, HO

    Potrebbero piacerti anche