A new one-pot and divergent synthesis of multisubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/ Corey-Chaykovsky epoxidation reaction was developed. The four-component reactions of 2-acylanilines, aldehydes, (carboxymethyl)(dimethyl)sulfonium bromides...
A new efficient synthesis of polysubstituted
pyrazin-2(1H)-ones via the sequential Ugi/Staudinger/aza-Wittig/isomerization
reaction has been developed. The four-component Ugi reactions of arylglyoxals 1, primary amines 2, α-azidovinyl acids 3, and isocyanides 4 produced the azides 5, which were treated with triphenylphosphine to give pyrazin-2(1H)-ones 6 in good yields through domino Staudinger/aza-Wittig/isomerization
reactions.
A new efficient and stereoselective synthesis of 12-tetrazolyl
substituted (E)-5H-quinazolino[3,2-a]quinazolines via sequential Ugi-azide/Staudinger/aza-Wittig/addition/Ag(I)-catalyzed
cyclization was developed. The four-component reactions of 2-azidobenzaldehyde,
2-(alkynyl)benzenamine, isocyanide, and trimethylsilyl azide gave
Ugi-azide intermediates, which were subsequently treated with triphenylphosphine
and isocyanate to produce 12-tetrazolyl substituted (E)-5H-quinazolino[3,2-a]quinazolines
in the presence of Ag(I) catalyst and K2CO3.
A new efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4H-3,1-benzothiazines via sequential Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reaction has been developed. The three-component Passerini reactions of 2-azidobenzaldehydes 1, benzoic acid (2), and isocyanides 3 produced the azide intermediates 4, which were treated sequentially with triphenylphosphine, isocyanates (or CS2), and secondary amines to give polysubstituted 3,4-dihydroquinazolines 8 and 4H-3,1-benzothiazines 11 in good overall yields through consecutive Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reactions.
A new efficient synthesis of 6,12-dihydro-5H-quinazolino[3,2-a]quinazolin-5-ones by sequential Ugi/Staudinger/aza-Wittig/addition/nucleophilic acyl substitution has been developed. -Amino amides 4, obtained from Ugi-3CR of 2-azidobenzaldehydes, methyl 2-aminobenzoates and isocyanides in the presence of catalytic amount of phenylphosphinic acid, reacted with triphenyl phosphine and isocyanates to give 6,12-dihydro-5H-quinazolino[3,2-a]quinazolin-5-ones 8 in good yields. This method provide a domino and effictive strategy for preparation of various substituted quinazolino[3,2-a]quinazolin-5-ones under mild reaction condition.
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