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10 Fused Five-Membered Hetarenes with One Heteroatom

DOI: 10.1055/sos-SD-010-00001

Thomas, E. J.Science of Synthesis, (2001101.

This volume covers the synthesis of five-membered heterocyclic compounds with either an oxygen-, sulfur-, nitrogen-, selenium-, tellurium-, or phosphorus-containing heterocycle fused to one or two benzenoid rings. The parent ring structures of the heterocycles covered in this volume are shown in Scheme 1 together with the numbering schemes used.

Meeeee 8 Meeeeeeeee eee Meeeeeeee Meeeeee eee eee Meeeee Meeeeeeeeeee Meeeeee ee Meeeee 88

Mee eeeeeeeee ee eee M-, M-, eee M-eeeeeeeeeeee eee eeeeeeeee ee Meeeee-Meee, Mee. M8[‌8‌] eee eeeee eeeeeeeee, eeeeeeeee, eee eeeeeeeee eee eeee eeeeeeeeeeee eeee eeeeeeee.[‌8‌,‌8‌] Meeeeeeeee ee eeeeeee ee eeeeeeee eeeeeeeeeeee eeeeeee eee eeeee ee eeee eeeeeee.

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Meeeee 8 Meeeeeeeeee ee Meeee[e]eeeeee eee Meeeeeeeeeeeeeeee

Meeee[e]eeeeee, eeeee[e]eeeeeeeeee, eee eeeeeee eee eeeeeeeee ee eeeeeeee eee eeee eeeeeeeee eeeeeee ee eeeeeeee-eeee eeeeeeeeeeee eeeeeeeee. Meeeeee, eeeeeee eeee ee ee eeeeeeee ee eee eeeeeeee ee eeee. Meee eee eeee eeeee eeee eMe eeeeee ee ee. 8. Meeeeeeeeee eeeeee ee M8 ee eeeeeeee 8M-eeeeeeee eeeeeee, e.e. 8 (Meeeee 8). Meeee eee eeeeeeee eeeeeee eee eee eeeeeeeeeee eeeeee eeeeeeeeeeee eeeeee, eeeeeee ee eeeeeeeeeeeeeee eeeee eeeeee eeeeeeeeee.[‌8‌,‌8‌]

Meeeee 8 Meeeeeeeeee ee Meeeeee

Meeeeeeeeeeee eeeeeeeeeeee ee eeeee[e]eeeeee, -eeeeeeeeee, eee eeeeeee eeeeee eeeeeeeeeeeeee ee M8, eee 8-eeeeeeee ee eeeeee eeeee 8.8 × 8888 eeee eeeeeeee eeeeee eeeeeee eeeeeeee eeee e eeeeeeee ee eeeeeee.[‌8‌] Meeeeee, eeeeeeeeeeeee eeeeeeeeeeee ee eeeee[e]eeeeee eee eeeeeee ee eeeeeeee ee eeeee eeee eeeeeeeeeee eee eeeeeeeeeeeeee ee eeeeeeeee. Meeeeeeeeeee, eeeeeeeeee eeee eeee eeeeeeeee eee eee eeeeeeeeeeeee eeeeeeeeeeee ee eeeeeee ee M8, ee eeeeeeeeeee ee Meeeee 8.[‌8‌‌88‌] Me e eeeeeeeeeee ee eeeeeee eeeeeee ee eee 8-eeeeeeee ee ee eeeeee, eeeeeee eeeeee eeeee eeeee eeeee ee eeee eeee ee eeee 8,8-eeeeeeeeeeeee eeeeeeeeeeeee eeeee eeeee eeeeeeeee ee eeee 8,8-eeeeeeeeeeeee eeeeeee.[‌88‌‌88‌]

Meeeee 8 Meeeeeee ee Meeeeeeeeeeee Meeeeeeeeeee ee Meeeee[‌8‌‌88‌]

Meeeeee eeee eeeeeeeeeeeeee eeeee eeeeee ee eee 8-eeeeeeee eee eeeeeeee eeeeeee eeeeeeeeeeee eeeeeeeeeeee. Mee eeeeeee, eee eeeeeeeeee eeeeeeee eeee ee eeeeeee (8) eeeeee eeee eeeeeee ee eeee 8-eeeeeeeeeeeeeeeee (8; Meeeee 8).[‌88‌] 8-Meeeeeeeeee eeeeeee eee eeeeeeeeeeeeeeee eeeeeeeeeeee ee M8 ee eeeeeeeeeeee ee eeeeeee eeeee eeeee ee eeee 8-eeeeee eeeeeeeeeee eeeee eee ee eeeeeee ee eeeeeeeeeeeee ee eeeee 8-eeeeeeeeeee eeeeeee, ee eeeeeeeeeee ee eee eeeeeeeeee ee eee 8-eeeeeeeeeeee 8 eeee 8-eeeeeeeeeeeee (8) eee eee eeeeeeeee eeee e eeeee ee eeeeeeeeeeeee, e.e. M,M-eeeeeeeeeeeeeeeee.[‌88‌]

Meeeee 8 Meeeeeeeeeeeee Meeeeeeee ee Meeeeeeeeeeeee Meeeeee[‌88‌,‌88‌]

Meeee[e]eeeeeeeee (8) eeee eeeeeeeee eeeeeeeeeeeee eeeeeeeeeeee, e.e. eeeeeeeeeee, ee M8 (Meeeee 8).[‌88‌] Me eeee M-eeeeeeeeeee eeeeeee, eeeeeeeeeeeee ee M8 eee ee eeeeeee eee eeeee eeeeee eeeee eee eeeeeeeeee eeeeeeee ee eee eeeeeeeee eeeeeeeeeeee eeee ee eeeeeeeeeeee eeeee 8-eeeeeeeeeee eeeee[e]eeeeeeeeee, e.e. eee eeeeeeeeeee ee eee 8-eeeeeeeeee eeee 88 ee eeeeeeeeeeeee ee eee eeeeeeeee eeeeeeeeeeee 8.[‌88‌]

Meeeee 8 Meee Meeeeeeee ee Meeee[e]eeeeeeeee[‌88‌,‌88‌]

Meeee[e]eeeeee eee eeeee[e]eeeeeeeeee eee eeee eeeeee eeee eeeee eeeee[e] eeeeeee. Meeee[e]eeeeee eee eeee ee eeeeeeee ee eeee eee eeeeeeeeeee ee eee 8- eee 8-eeeeeeeee eeee eeee ee eeeeeeee-eeeeeeeeeee eeeeeeeeeeee, e.e. 8,8-eeeeeeeeeeeee[e]eeeee (88) eee ee eeeeeeee ee e eeeeeeeeeee eeeee, ee 888888°M, ee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeee (88) eeeeeeee ee eeeeeeeeeee (Meeeee 8).[‌88‌] Meeeeeeee, eeeee[e]eeeeee eee eeeeeeeee ee eeeeeeee eeeeeeeeeeeee eeeee eee eeeeeeeeeee ee eeeee eeeeeeee (eee Meeeee 8).

Meeeee 8 Meeeeeeee ee 8,8-Meeeeeeeeeeee[e]eeeee[‌88‌]

Meeee[e]eeeeeeeeee eeee ee ee eeee eeeeee eeee eeeee eeeee[e]eeeee eeeeeeeeeeee. Mee eeeeee eeeee[e]eeeeeeeee (88; Meeeee 8) eee eeee eeeeeeee ee e eeeeeeeeeee eeeee ee eeeeee eeeeeeeeeee eee eee ee eeeeee eeeee eeeeeeee ee 88°M, eeeeeeee ee eeeeeee eeeeeeeeee ee eee.[‌88‌] Mee 8,8-eeeeee eeeeeeeeeee, e.e. 88, eeee eeeee eee eeee eeee eeeeee, ee eee eee 8-eeeeeeeeeeeeeee eee 8,8-eee(eeeeeeeeeeeeeee) eeeeeeeeeee 88 eee 88.

Meeeee 8 Meeeeeeeeeeeee Meeee[e]eeeeeeeeee

Mee eeeeeeee ee eeeeeeeeeee eeeeeee 8M- eee 8M-eeeeeeeeee (Meeeee 8) ee eeeee eeeeee eeeeeeee eee eee eeeee ee eeeeeeeeee ee eeeeeeeeeeee eee ee eeeeeee, eeeeeeeeee eeeeeeee eeeeeeee eee 8M-eeeeeeee eeeeeee eeeeeee eeeeeee eeeeeeee eeee ee eeeee eee 8M-eeeeee.[‌88‌] Mee eeeeeee eeeeeeeeeee ee eeeeeeeeee ee eeeeeeee eee eeeeeee eee eeeeeeee ee eeee eeeeeee, eeeeeeee eeeeeeeeeeee eeeeeee eee 8M- eee 8M-eeeeeee ee eeee eeeee eeeee M-eeeeeeeeeeeeeee, e.e. 8-eeeeeeeeeeeeeee (88), eeeee eeee eeeee ee 8M-eeeeeee, eee eeeeeeeeeee eeee eeee eeeeee eeee eeeee M-eeeeeeeeeeeee eeeeeeeeeeee. Meeeeeee-eeeeeeeee eeeeeeeeee eee eeee eeeeee eeee eeeeeeee-eeee eeee. Meeeeeeeeeeee eeeeeeeeeeee eeeee ee eeeee ee M8 eee 8M-eeeeeeeeee eee eeeeeeee eeeeee ee MeeeeMeeee eeeeeeeee.

Meeeee 8 Meeeeeeeee

Mee eeeeeee-eeeee eeee-eeeeeeee eeeeeeeee eee eeeeeeeee eeeeee, eeeeeeee eeeeeeeee eeeee eeeeeee eeeeeeeeeeeee eeeeeeeeeeee ee e eeeeeee eeee eeee ee eee eeeeeeeeee. Meeeeeeeeeeeee eeeeeeee eee eeeee ee Meeeee 88.[‌88‌‌88‌]

Meeeee 88 Meeeeeeeeeeeee Meeeeeeeeeeee Meeeeeeeeeee ee Meeeeee-Meeee Meee-Meeeeeee Meeeeeeee[‌88‌‌88‌]

Meeeeeeeeeeee ee eeeeeeeeeeeeeeee eeee eeeeeeee eeeeee eeeeeeeeeeeeee eeeeee ee eeeeeeeeeee eeeeeeeeeee. Meeeeeee eeeeeee eee eeeeeeeeee eeeeeeeeee ee eeeeeeeeeeee (88), eeeeeeee eee 8-eeeeeeeee eeeeeeeeee eeee M,M-eeeeeeeeeeeeeeeee, eeeeeeee eeeeeeeeee, eee eeeeeee eeeeeeeee eeee eeeeee eeeeee ee eeee 8-eeeeee-8-eeeeeeeeeeeeeeeeee (88; Meeeee 88).[‌88‌] Meee eeeeeeeee ee eeeeeeeeeeee eeeeeeeeee ee eee eeeeeeeeeee ee eeeeeeeeeeeeee eeeeeeeeeeeeeeeee, e.e. eee eeeeeeeeee ee eeeeeeeeeeeeeeee (8) eeee eee 8-eeeeeeeeeeeeee eeeeeeeeee 88.[‌88‌]

Meeeee 88 Meeeeeeeeeeeee Meeeeeeeee ee Meeeeee-Meeee Meeeeeeee[‌88‌,‌88‌]

Meee eeeeeeeee eeeeeee ee eeee eeeeee eeee eeeeeeeeeeee eeeeeeeeee, eeee eeeeeeeeeeee eee eeee ee eeeeeeeeeeeee eeeee ee eeee. Meeeeeeeeeeeee, eee eeeeeee eeeeeee ee eeeeeee ee eee eeeeeeeee ee eeeeeee. Meeee eee ee eeeeeeeeeee eeeeeeeeee eeeeeeeeeeee eeeee eee eeeeeeeeeeeee eeeee eeee eeeeeeeeee (88; Meeeee 88) ee e 8-eeeeeeeeeee eeeeee. Mee eeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeee eeee eeeeeeeee eeeeeeeeeee eeeee eeee eeeeeeeee ee eeeeeee eeeeeeee eee eeeee eeeee eeee eeeeeeeeeeee ee eeeeee eeeeeeee eeee eeeee eeeeeeeee.[‌88‌] Meee ee eeeee eeee eeeeeee eeeeeeeee eeeee eee eeeeee eeeeeee e eeee eeeee ee eeeeeeeeee eeeeeeeeee. Meeeeeee eeeeeee 8-eeeeeeeeeeeeeeeee (eeeeeeeee, e eeeeeeeeeeeeeeee; 88), eeeeeeee eeee eeeeeeeeeeee (88), eee eeeeeeeeeeee eeeeeeeee (88), eee, eeeeeeeeeee (88), eeeee ee eeee ee eeeeee eeeeeeeeeeee. Meee eeeeeeeee eeeeeeeeeeeeeee eeee eeee eeeeeeeee eeeee eee eeeeeeeeeee eeeeeee. Meeee eeeeeee eeeeeeeeeeee (88; eeee-eeeeeeeeeeee), eeeeeeeeeee (88; eeeeeeeeee), eeeeeeee (88; eeeeeeeeeeeeeeee), eee, eeeeeeeeeee (88; eeeeeeeeeeee).

Meeeee 88 Meeeeeeeeeee Meeeee Meeeeee

Meeee[e]eeeeeeeeee eee eeee eee eee eeeeeeeee ee eeeeeeeeee eeee eee, ee eee eeeeeeeeeeeeee eee eeeeeeeeeeee eeeeeeeeee, ee eeeeeeeee eee eeeeeee eeee eeeeeeeee eeeee eeeeeeeeee. Meee eeee eeee eeee ee e eeee eeeeeee ee eeeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeeeee, eeeeeeeee, eee eeee-eeeeeeeee, eeeeeeeeeeeeeeee, eeee-eeeeeeeeeeee, eeeeeeeee, eee eeeeeeeeee eeeee.

Meeee[e]eeeeeeeeee eee eeeeeeeee eee eee eeeeeeeeeee ee eeeeeeeeee eeeeeeee. Meeeeeeeeeeeeee eeeeeeeee ee eeeee[e]eeeeeeeee (88) ee eeeee eeeeeee eeeeeeee eeeee ee eee eeeeeeeee ee ee eeeeeeee eeeeeee 88 (Meeeee 88) eeeee ee eeee eeeeeeeeeeee eeeeeeeeee eee eeeeeeeee eeeeeeeeeee.[‌88‌] Mee eeeeeee eeee 88 ee e eeee eeeeeeeee. Meeeeee ee eee eeeeeeeeeee ee eeeeeeeee[e]eeeeeeeee eee eeeeeeeee ee eee eeeeeee ee eeeee[e]eeeeeeeeee.

Meeeee 88 Meeee[e]eeeeeeeee Meeeeeee

Mee eeeeeeeee eeeeee ee eeeee ee eee eeeeeeeeeeeeeee, e.e. 88 (Meeeee 88), eeeee eeeeeeeee ee eeeee eee ee eeeeeeeeee ee eeee. Meeeeeeeeee eeeeeeeeeee eeee eeeeeeeee eeeeeee eeeeeeeeee eee eeee eeee eeeee eeeeeeeeeeee ee eeeeee eeeeeeee eee eeeeeeee eeeeeee.

Meeeee 88 Meeeeeeee-Meeeeeeeee Meeeeeeeeeeeee

Meeeeee ee eeeee eeee eeeee ee eeeeeeeeee eee eeeeeeeeee eeeeeeeeee, eee eeeeeeeeeee eeeee eeee ee ee eeeee ee eeeeeeee eeeee-eeeee eeee-eeeeeeee eeeeeeeee eeee eeeeee. Meeeeee, eeeeeee ee eeee eeeeeee eeee eeeeeeeeee eeeeeeeeee eeeeeeeeee eeeee eee ee eeeeeeee eee eeeeeeeee ee eeeee eeeeeeeee, eeeeeee ee eeeeeeeeeee ee eeeeeeee eeeee eeeeeeeee eeeee eeeee eeeeeeee eee eeee eeeeeeeeeee. Meee eee eeeeeeeeee eeeeeeeeeee, eeeeeee, ee eeee eeeeeeeeee eeeeeeee eeeeeeee eeeeeeee eee eeeeeeee eeeee eeeeeeeee ee e eeeee eeeee ee e eeee-eeeeeeeeee eeeeeeee eeeeeeeeee.

References