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10.21.1.4.1.4.1.1 Formation of C-Hydrogen Compounds

DOI: 10.1055/sos-SD-110-00324

Stanforth, S. P.Science of Synthesis Knowledge Updates, (2014363.

Ester derivatives of hetaryl[3,2-b]hetarenes are readily available through a variety of annulation routes (see Section 10.21.1.1.1 and subsections therein). Hydrolysis of these esters affords the corresponding carboxylic acid derivatives, which can be readily decarboxylated in good yield, generally by heating in quinoline at reflux in the presence of copper (Table 4).

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Meeee Meeeeeee Meeeeeee Meeeeeeeee Meeeeee Meeee (%) Mee
8 Me, eeeeeeeee, 888 °M, 8 e e [‌888‌]
8 Me8Me8M8, eeeeeeeee, 888–888 °M 88 [‌88‌]
8 Me, eeeeeeeee, 888 °M 88 [‌88‌]
8 Me, eeeeeeeee, eeeeee 88 [‌888‌]
8 MMM/MMM,e 888–888 °M, 8 e 88 [‌888‌]
8 ee MMe, eM 8, eeeeee, 88 e 88 [‌888‌]
8 Me, eeeeeeeee, 888 °M, 88 eee 88 [‌88‌]
8 Me, eeeeeeeee, eeeeee, 8 e 88 [‌88‌]
8 Me, eeeeeeeee, eeee 88 [‌88‌]
88 Me, eeeeeeeee, eeee 88 [‌88‌]
88 Me, eeeeeeeee, eeeeee, 8 e 88 [‌88‌]
88 Me, eeeeeeeee, eeeeee 88 [‌88‌]
88 Me8Me8M8, eeeeeeeee, 888 °M 88 [‌88‌]
88 Me, eeeeeeeee, 888–888 °M, 88 eee 88 [‌888‌]
88 Me8Me8M8, eeeeeeeee, 888 °M 88 [‌88‌]

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Meeeeeeeeee 88

Me8 Me8 Meeee (%) Mee
Me Me 88 [‌88‌]
8-MeMM8M8 8-MeMM8M8 88 [‌88‌]
8,8-(MeM)8M8M8 8,8-(MeM)8M8M8 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8M-Meeeee[8,8-e]eeeeeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

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8-Meeeeeeeeee[8,8-e]eeeeeeeee (Meeee 8, Meeee 8); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee 8-eeeeeeeeeee[8,8-e]eeeeeeeee-8-eeeeeeeeee eeee (88.8 e, 88.8 eeee), Me (~88 µe eeeeee, 8.88 e, 888 eeee), eee eeeeeeeee (88 eM) eee eeeeee ee eeeeee eee 8 e. Mee eeeeeee eeeeee eee eeeeeee ee 8 eM ee eeeeeeeeeeee (88 Meee). MeMMe (888 eM) eee eeeee ee eee eeeeeee, eee eee eeeeeee eeeee eee eeeeee eeee 8 M ee MMe (8 × 888 eM) eee eeeee (Me8MM8). Mee eeeeeee eee eeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee); eeeee: 88.8 e (88%).

8,8-Meeeeeeeeeeeee[8,8-e][8,8-e]-8,8-eeeeeeee-8-eeee-8e,8e-eeeee-e-eeeeeeee (888, Me8 = Me8 = Me); Meeeeee Meeeeeeee:[‌88‌]

8-Meeeee-8M-eeee[8,8-e]eeeeeee-8-eeeeeeeeee eeee (888, Me8 = Me; 88.8 ee, 8.888 eeee) eee eeeeeeeee ee MMM (8 eM) eee eeeeee ee 88 °M eee 88 eee. 8-Meeeee-8M-eeee[8,8-e]eeeeeee-8-eeeeeeeeeeee (888, Me8 = Me; 88.8 ee, 8.888 eeee) eee MMMe8 (8.8 eM) eeee eeeee. Mee eeeeeee eee eeeeeee eee e eeeeeee 88 eee eeeee ee eeeeeee eeeee (eeeee eee eeeeeeeee) eee eeeeee. Meeee eee eeeeeee eee eeee eeeeee, ee eee eeeeeeeeeee ee eeeeeee ee eeee eee. ee MeMMM8. Mee eeeeeeeee eeeeeeeeeee eee eeeeeeeee, eeeeee eeee M8M, eee eeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeee eeeeeeee eee eeeeeeeee ee 8,8,8-eeeeeeeeeeeeeee (88 eM), eee MM8•MMe8 (8.8 eM) eee Me8M (8.8 eM) eeee eeeee. Mee eeeeeee eee eeeeeee ee 888 °M eee 88 eee. Meeee eee eeeeeee eee eeee eeeeee, ee eee eeeeeee eeee MMMe8. Mee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee eee. ee MeMMM8 eee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MMMe8), eeeeee eee eeeeeee ee e eeeee eeeeeeee eeeee; eeeee: 88.8 ee (88%).

References


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