AN ALTERNATIVE APPROACH TO THE SYNTHESIS OF 5 H -CHROMENO[4,3- b ]PYRIDIN-5-ONE SYSTEM USING THE CLEAVAGE OF 5 H ,9 H -PYRANO[2',3':5,6]CHROMENO[4,3- b ]PYRIDINE-5,9-DIONES WITH BINUCLEOPHILES

Oleg A. Lozinski; Tatyana V. Shokol; Roman I. Zubatyuk; Oleg V. Shishkin; Volodymir P. Khilya

doi:10.1007/4211

AN ALTERNATIVE APPROACH TO THE SYNTHESIS OF 5H-CHROMENO[4,3-b]PYRIDIN-5-ONE SYSTEM USING THE CLEAVAGE OF 5H,9H-PYRANO[2',3':5,6]CHROMENO[4,3-b]PYRIDINE-5,9-DIONES WITH BINUCLEOPHILES

Oleg A. Lozinski, Tatyana V. Shokol, Roman I. Zubatyuk, Oleg V. Shishkin, Volodymir P. Khilya

Abstract

Hantzsch reaction has been successfully employed for a one-step assembling of pyranopyridine fragment to produce 5Н,9Н-pyrano[2',3':5,6]chromeno[4,3-b]pyridine-5,9-diones which upon treatment with binucleophiles undergo chemoselective γ-pyrone ring opening with the concomitant recyclization to give five-membered cycles, providing a concise route to 6-pyrazolyl(isoxazolyl)-5H-chromeno[4,3-b]pyridin-5-ones.

Keywords

carbonyl compounds; condensed chromones; isoxazoles,; pyrazoles; cyclization; recyclization

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Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv

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