abstract
The reaction of indole derivatives with cyanoacetic acid followed by treatment with DMFDMA gave the intermediate indolyl enaminonitriles 3. Further reaction with aminoguanidine yielded 5'-cyanomeridianin analogues 4. The same intermediate reacted with p-methoxyphenylhydrazine to give the pyrazolyl derivative 8. Treatment of (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate 3a with hydroxylamine hydrochloride in basic medium afforded (5-amino-isoxazol-4-yl)-(1H-indol-3-yl)-methanone 5 and the acrylic acid derivative 6 after a short or a long heating, respectively. Unequivocal structural elucidation of the latter compound was achieved from single-crystal X-ray diffraction studies.
keywords
TUNICATE APLIDIUM-MERIDIANUM; ANALOGS; 3-HETEROARYLINDOLES; INDOLYLPYRIMIDINES; ACRYLONITRILE; ALKALOIDS; ACID
subject category
Chemistry
authors
Oliveira-Campos, AMF; Salaheldin, AM; Paz, FAA; Rodriguesa, LM
our authors
Filipe Alexandre Almeida Paz
Principal Researcheracknowledgements
We are grateful to Fundacao para a Ciencia e a Tecnologia and FEDER (POCTI-SFA-3-686, for general financial support; REEQ/ 630/QUI/2005, for LCMS; and specific funding for the purchase of the single-crystal diffractometer). We also acknowledge FCT for funds to support the NMR spectrometer as part of the National NMR Network (RNRMN). Thanks are due also for the post-doctoral research grant to A. Salaheldin (SFRH/BPD/31490/2006). We further thank Miss Elisa Pinto for obtaining the NMR and elemental analyses data, and Miss Natercia Nunes for LCMS determinations.