4.2 Article

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

Journal

MENDELEEV COMMUNICATIONS
Volume 25, Issue 5, Pages 329-331

Publisher

ELSEVIER SCIENCE BV
DOI: 10.1016/j.mencom.2015.09.002

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Funding

  1. Russian Foundation for Basic Research [15-03-08195A]

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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-1,2,3,3 a,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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