One-Pot Synthesis of 1-Arylmethylidene-1,2,3,3a-tetrahydro-5H-pyrrolo[1,2-a] [3,1]benzoxazines and 1-Arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinazolines from 5-Arylalk-4-ynals and o-Aminobenzylic Alcohol/Amine.

ChemInform(2016)

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摘要
Cyclization of 5-arylalk-4-ynals with o-aminobenzylamine or o-aminobenzyl alcohol in DMSO under the sequential action of NH4Br and KOH affords (E)-1-arylmethylidene-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinazolines or (E)-1-arylmethylidene-1,2,3,3a-tetrahydro- 5H-pyrrolo-[1,2-a][3,1]benzoxazines; the latter without substituents in the 3-position easily isomerize into the corresponding 2-arylmethyl- 1-(2-hydroxymethylphenyl)pyrroles.
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