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14 Six-Membered Hetarenes with One Chalcogen

DOI: 10.1055/sos-SD-014-00001

Thomas, E. J.Science of Synthesis, (2003141.

General Introduction

Six-membered oxygen containing heterocycles are an important group of compounds widely dispersed throughout the plant kingdom. They are components of many biologically active compounds including drugs. This volume of Science of Synthesis covers the synthesis of six-membered hetarenes with one chalcogen, i.e. oxygen, sulfur, selenium, or tellurium, in the heterocyclic ring, including pyrylium salts and pyranones together with their benzo-fused analogues.

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Meeeeeee eeeee eeee eee-eeeeeeeeeeee eeeeeeeeeee eee eeeeeeeee ee eeeeeeee eeeeeeee ee eeeeeeeeee eeeeeeee eeee eee eeee eeeeeeeeee ee e eeeeeee eeeeeee. Meeeeeeeee eeee eeeeee ee eeeeee eeeeeee eeeee eee eee eeee eeeeee, e.e. ee eeeeeeeeee ee eeeeeee eeeeeeee, eeee eeeeee eeeeeee eeeee, eeeeeeeeee ee eeee eeeeeeee eeeeeeeee.[‌8‌] Mee eeeeeeee ee e eeeeeeeeeee eeee eeeeeee ee eeeeeeeee ee MMM, eee Meeeee 8, eee MM eeee.[‌8‌‌8‌] Meeeeeeeeeee eeeee eee eeee eeeeee eeee eeeee eeeeee ee eeeeeeee eeeeeeeee.[‌8‌‌8‌]

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Meeeeeee eeeee eee eeeeeeeeeee ee eeee-eeeeeeeee eeeeeeeeee eeeeee MM eeeeeee 8 eee eeeeeeeee 8 eee eeeeee ee eee 8- ee 8-eeeeeeeee, eee Meeeee 8; eeeeeeeeeeee ee eeeee eeeeeeeee eeee ee eeeeeeeee eeeeeeeee.[‌8‌] Meeeeeeee eeee eeeeeee eeeeee ee eeeeeeeeeeeeee eeeeeeee eeee eeeeeee eeeeee ee M8 (M8) eeeeeeee ee eeee-eeeeeee, eeeeeeeeeee, eee eeee eeeeeee, ee eeee eeeeeeeee eeeeeeeee ee eeeeeeeeee eeeee, e.e. 8. MMM eee MM eeee eee eeeeeeeeeeeee eee eeeeeeeeee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeee eeee eeeeeeee ee eeeee eeeeeee eeee eeeeeeeee eeeeee eeeeeeeeeeeeee eeee eee eeeee,[‌8‌,‌8‌] eee eeeeeeeeeeee eeeeee eeeeee ee eee eeeeeeeeee eeee ee eeeeeeee eee eeeeeeeee ee eee eeeeeeeee eeeee, e.e eee eeeeeeee ee eeeeeeeeee ee eeeeeeeeee eeee 88 ee M8.[‌88‌]

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Meeeeee eeeeeeeee eeeeee ee eeeeeeee ee eeeeeeee eee eeee eeeeeeeeeeee eeeeeeeeeee eeee eeeeeeeeeeeee eee eeeeeeeeeeeeee.[‌8‌,‌8‌] Mee 8M eee 88MMMM eeeeeee ee 8M-eeeee-8-eee (8) (Meeeee 8) eeee eeeeee eeeeeeee ee e eeeeeeeeeee eeee eeeeeee eee eeeeeeee eeeeeeee eeee eee eeeeeeeeee eeee eeee eeeeeeeeeeee.[‌88‌‌88‌] Mee MM eeeeeeee eeeeeeeeee eeeeeeeeeee ee 8M-eeeee-8-eeee (ee. 88888888ee8) eee eeeeeee ee eee-eeeeeeee eeeeeeee eeeeeeee e eeeeeee eeeeeeeeeeee eeee eee eeeeeee eeeeeeeee 8. Meeeeee, MMM eee MM eeee eee 8M-eeeee-8-eeee, e.e. e M=M eeeeeee ee eee eeeeee ee 88888888ee8, eee eeeeeeeeee eeee e eeeee eeee eeeeeee eee eeee eeeeeeeeeeeeee. 8M-Meeee-8-eee ee eeee eeeee eeee eeeeee eeeeeee eeee e eMe ee 8.8 eee 8M-8-eeeeeeeeee-8-eee (88), eeee e eMe 8.8, ee eeee eeee eeeee. Mee 8M-eeeee-8-eeeeee (88), eeeeeeeee eeeeeeeeeeee eeeee e eeeeeee eeeeeeeeee ee eee M8M8 eeee eee eeeeeeeeeee ee eee M8M8 eeee eeeeeeeeee ee eeeeeeee eeeeeeeeeee.[‌88‌]

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Mee eeeeeeeee ee 8M-eeeee-8-eeee eeeeeeeee eeeeeeee eeee eeeee eee eeee eeeeeee eeeeeeeee. Meeeeeeeeee ee 8M-eeeee-8-eee (8) eeeee 8M-8-eeeeeeeeee-8-eee (88) eee eeeeeeee ee eeeeeee eeeeee eee 8,8-eeeeee eeee eeeeeeee ee eeeeeeeeeeeeeeeeee.[‌88‌] Meeeeee, eeeeeeeeeeee eeeeeeeeeeee ee eeeeeeee, eeeeeeeee ee 8M-8-eeeeeeeeeee-8-eee (88) eeeeee eee 8-eeeeeeeeeeee 88 ee 88% eeeeee eeee ee eeee. Meee eeeeeeee eeeeee eeee, eeeeeeeee eeeee eeeee ee eee eeeeee eeee eeeeeee eeeeeeee eeeeeeeeeee eeeeeee eee eeeeeeeeee ee eee eeeeeeee eeeeeee eeeeeeeeeeeee eeeeee.[‌88‌] Meeeeeeee ee 8M-eeeee-8-eee 8 eeee eeeeeeeeeeeeeeee eeeeeeeeeeeeeeeee eeeee 8-eeeeeeeeeeeeeee eeeeeeeeeeeeeeeee (88). Meeeeeeeeeee eeeee eeee 8M-eeeee-8-eeee ee eee eeeeeee eeeee eeeeeee ee eeee eeeeeee, eee eeeeeee eeeee eeee eeeeee eeeeeeeee eee MeeeeMeeee eeeeeeeee, eeeee eee eeee eeeeeeeee eeeeeeeeeee ee eeeeeeeeee eeee ee eeeeee eeeeeee.[‌88‌] Mee eeeeeee, eeeeee 8-eee-8M-eeeee-8-eeeeeeeeeee (88) eeeee eeeeeeeee eeeeeee-8,8,8-eeeeeeeeeeeeee (88) ee eeeeeee eeee eeeeeeee eeeeeeeeeeeeeeeeeeeeee. Meeeeeeeee ee 8M-eeeee-8-eeee eee eeee eeeeee eeeeeee eeee eeeeeeeeeee ee eeeeeeeeeeee, e.e. 88, eeeeeeee eeeee eeeeeee eeeeeeeeee (Meeeee 8).[‌88‌,‌88‌]

Meeeeeeeeee ee eeeeeeee eeee eeeeeeeeeee eeeeee, eeeeeeee 8M-eeeee-8-eee (8) eeee 8-eeeeeee- ee 8-eeeeeeeeeeeeeee eeeee, e.e. 88. Meeeeeeee eeee eeeeeeeeeeeeee eeeeeeee eeee eeeee ee M8 eeeeee 8-eeeeeeeeeeeee eeeee eeeee eeeeeeeeee eeeeeeeeeee, e.e. 88, ee 8M-8,8-eeeeeeeeeeeee (e.e., eeeeeeeeee ee 8,8-eeeeeeee-8M-eeeee-8-eee 88 eeee eee 8,8-eeeeeeee eeeeeeeeee 88) ee ee eeeeee ee eee eeeeeeeeeeeeee eeeeeee ee eeee. 8M-Meeee-8-eeee eeeee eeee M- eee M-eeeeeeeeeeee ee eeee M8, eeee eeee eeeeeee, eee ee M8 eee eee eeee eeeeeeee ee eeeeeeee. Meeeeeeeee ee 8M-eeeee-8-eee (8) eeeee 8M-eeeee-8-eee (8) eee e π-eeeeeeeee eeee ee eeeeeeeeeeeee (Meeeee 8).[‌88‌]

Meeeee 8 Meee Meeeeeeee ee 8M-Meeee-8-eeee eee 8M-Meeee-8-eeee[‌8‌,‌8‌,‌88‌‌88‌]

Mee eeee eeee ee eeeeeeeeee eeeeeeee eeeee eeeeeee eeeee eeeeeee eeeeeeeeee. Mee eeeeeee, eee eeeeee eeeeeeeeeeee ee 8,8,8-eeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeee (88) (Meeeee 8), eeeee ee eeeeeeeeeeee eeeeeeeee, eee eeee eeeee eee e eeee eeee, eee eeee eeee ee eeeeee eeee ee e eeeeeeeeeeeeeee ee eeeeeeee-eeeeeeee eeeeeeeee.[‌88‌] 8-Meeeeeeeeeeee eeeee eeee eeee ee eeeeeeeeeeee eeeeeeee eeeee ee eee eeeeeeeeee eeee eeee ee eee eeeeee ee eeeeeee eee eee ee eee 8-M-eeeeeeeeee ee eeeeeeeeeee eeeeeeeee (e.e., 8-eeee-8-eeeeeeeeeeeee) eeeee, e.e. eeeeeeeeeeeee.[‌88‌] Meeeeeeeeeee eeeee eee eeeee eeeeeeee eee eee eeeeeeeee eeeeeeeee eeee eeee eeee eeeeeeeee eeeeeee ee eeeee eeeeeeeeeeeee eeeeeeeeee eee eeeeeeee eeeeeeeee ee eee eeeeeeeeeeee eeeeee.[‌8‌‌8‌]

Meeeeeee eeeee eee eeeee ee eeee eeeeeeeeee eeeeeee eeeeeeee eeeeeeeee eeeeeeeeee eeeeee eeeeeeeee eeee ee eee eeeeeeeeee eeeee eeee (88) ee eeee eeeeeee eeeeeeee, eeee ee eeeeeeeee (88). Meee ee eeeee eeeeeeeee, eee eeeee eeeeeeeee eeee eee eeeee eeeeeeeeee ee eee eeeeeeeeee eeeee, eeee eee eeeeeeeee ee ee eeeeeeeee eeee eeeeee eeeeeeeeeeeeeee, eeee ee eeeeeeee (88), eeeee ee eeee ee eeeeee eee eeeeeeee ee eeeee ee eeee (Meeeee 8). Meee eeee eeeeeee eeeeeeee, e.e. eee eeeeeeeeee eeeeee eeeeeee eeeeeeee, eeee eeeeeee eeeee eee eeeeeeee eeeeeeeeeeeee, eee eee ee eeeeeeee eeee eee eeeeeeeeeee eeeeeeeee ee eeee eeeeee.

Meeeee 8 Meeeeeee ee Meeeeeeeeeee Meeeeeeee eee Meeeeeeee Meeeeeeee Meeeeeee Meeee eee Meeeeeeee[‌88‌,‌88‌]

MMMMMM: Meee ee eee eeeeeeeeeeee eeeeeeeee ee eeee eeeeee eeee eeeeeeeeee eeeeeeee eee eeeeee ee eeeeeeee ee eeeee. Meeeeeeee eeee eeeeee ee eeeeeee eeee eeee eeeeeeee, ee eeee eeee ee ee eeeeeeeeee, eeee eeeeeeeeee eeeeeeee eeeeee eeeeeee. Meeeeee, eeeeeeeeee eeee eeee ee eeeee eeee eeeeeeee eeeeeeeeee eeee eee eeeeeeeeeee eeeee. Mee eeeeeeeee ee eeeeeeee eeeee ee eeeeeeeeeeee ee eeeeeeeeee eeeeeee ee eee eee-eeeeeeeeeeee eeeeee ee eee eeeeeeeeeee eeeee eee eee eeeee eeeeeeeee eeeeeeeeeeeee ee eee eeeeeeeeeeee. Meeeeee, eeeeeeeeee eeee ee eeee e eeeeeeee eeeeeeeee eeeee eee eee eeeeeeee eeee eeeeeee eeeeeeeeee eee eeee ee eeeeeeeeee. Mee eeeeeee eeeeeeeeeee eeee eeeeeeeee ee eeeeeee eeee eee eeeeeeee eeee eeeeee e eeeeee eeeeee eeeeee eee eeeeeee ee e eeeeeeeee eeeeeeeee. Me ee eeeeeeeeeee eeee eeeeeeeeeeeeeeeee eeeee eee eeee eeeeeeee eeeeeeee.

References


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