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Paper | Special issue | Vol 88, No. 2, 2014, pp.1149-1161
Published online, 26th September, 2013
DOI: 10.3987/COM-13-S(S)73
■ Aminophenylpyrrole Synthesis and Application to Pyrrolo[1,2-c]quinazolinone Synthesis

Aurélie A. Dörr and William D. Lubell*

*Department of Chemistry, University of Montreal, CP 6128, Succursale-Centre-Ville
Montreal, Quebec, H3C 3J7, Canada

Abstract

Aminophenylpyrroles have been synthesized by a three-step route from methyl N-(Boc)anthranilate (2). Amine protection of commercially available methyl anthranilate (1) gave Boc-protected methyl ester 2, which reacted with vinylmagnesium bromide in the presence of a catalytic amount of copper (I) cyanide to yield 1-[2-N-(Boc)aminophenyl]pent-4-en-1-one (3) in 43% yield. Oxidation of homoallylic ketone 3 using either a mixture of OsO4•NaIO4 and 2,6-lutidine, or PdCl2-CuCl under oxygen atmosphere gave respectively aldehyde 4 and ketone 5. Treatment of 1,4-dicarbonyl compounds 4 and 5 with ammonium formate as well as primary amines under Paal-Knorr conditions afforded a set of eight 2-[2-N-(Boc)aminophenyl]pyrroles 6a-d and 7a-d. In addition, treatment of 2-[2-N-(Boc)aminophenyl]-1H-pyrrole 6a with NaH provided a novel entry to pyrrolo[1,2-c]quinazolin-5(6H)-one 8.