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10.13.1.1.1.2.1.1.4 Variation 4: From 2-(o-Aminoaryl)acetaldehyde Acetals or Hemiacetals

DOI: 10.1055/sos-SD-010-00559

Joule, J. A.Science of Synthesis, (200110417.

Since palladium-catalyzed coupling methodology allows easy access to arenes 316 with an alkynyl substituent ortho to a nitro substituent, from o-iodo- or o-bromonitroarenes 315,[‌223‌,‌224‌] 2-(o-nitroaryl)acetaldehyde acetals 317 can also be viewed as easily obtained intermediates via subsequent reaction with alkoxides involving addition to the triple bond; nitro group reduction and acetal deprotection produces pyrrole-ring-unsubstituted indoles 318 (Scheme 88).

Meeeee 88 Meeeeee eeee (e-Meeeeeeee)eeeeeee eee 8-(e-Meeeeeeee)eeeeeeeeeeee Meeeeee[‌888‌,‌888‌]

Meeee 88 eeeeeeeeee eeeeeeee ee eeeeee ee ee eeeeeeeee, e-eeeeeeeeeeeeeeee eeeeeee Meee eeeeeeee eeeee eeeeeeeee(MM) eeeeeee/eee-8-eeeeeeeeeeeeee/eeeeeeeeeeeee/888°M eeeeeee ee eee eeeeeeeeeee ee eee eeeeeee eeee e eeeee eeeeeeeeeee. Me eeee eeeeeeeee, eeeeeeee ee eee eeeeeee eeeeeee eee eee eeeeeeeeeeeee eeeeee eee eeeeee.[‌888‌] Mee 8-eeeeeeeeeeeee 888 eee eeeeeeeee eeee eeeeeee eee (e-eeeeeeeee)eeeeeeeeeeee eeeeeee (Meeeeee 88 eee 88), eeee eeeeeeee eeee eeeeeeeee(MM) eeeeeeee/eeeeee(M) eeeeeeee/eeeeee/eeeeeee-8,8-eeee eeeeeeee 8-(e-eeeeeeeee)eeeeeeeeeeee eeeeeee-8,8-eeee eeeeeee 888 eee eeeeee eeeeeee 888 (Meeeee 88), ee e eeeeeeeeeeee ee eee Meeeee eeeeeeeee, eeeee eeeeee/eeeeeeee eeeeeeeeeeeeeeeeeeee(MM)/eeeee eeeeeee, eeeeeeee 888 eeee 8-(e-eeeeeeeee)eeeeeeeeeeee eeeeeee 888 (Meeeee 88) eeeeeeeeeeeee ee eee eeeee eeeee ee eee eeeeeee. Meeee eeeee eeeeeeeeeeeee, e.e. eeee eeeeeee/eeeeee, eeeee eeeeeee eeeeeeeee eeeeeeeee eeee eeeeee eeeeeeeeeeee eeee;[‌888‌] eeeeeeeeeeeee, eeeeeeeee eeee eeee/eeeeee eeee eeeeee eeeee eeee eeeee eeeee eeeeeeeee eee eeee-eeeeeeeee eeeeeee ee eee eeeeeeee eeeeeeee 888 ee eee eeee eee.

Meeeee 88 Meeeeee eeee (e-Meeeeeeee)eeeeeee eee (e-Meeeeeeee)eeeeeeeeeeee Meeeeee[‌888‌]

Meeeee 88 Meeeeee eeee (e-Meeeeeeee)eeeeeee eee (e-Meeeeeeee)eeeeeeeeeeee Meeeeee ee Meeeeeee Meeeee Meeeeeeee[‌888‌]

Mee eeeeeeeeeeee eeeeeeeeee ee eeeeeeeeeee eeee eeeee eeee eeeee eeeeeeeeeee ee eeeeee, eeeeeeee ee eeeeeeeee eeee eeeeeee ee 8,8-eeeeeeee-8,8-eeeeeeeeeeee-8,8-eeeeeee, ee e eeeee ee 8-(e-eeeeeeeee)eeeeeeee eeeeeeeeeee. Me ee eeeeeeeeeeee, Meeeee 88 eeeee eee eeee eeeeee ee eeeeeee ee eee eeeeeeeee ee 8-eeeeee-8M-eeeeee-8-eeeeeee (8-eeeeeeeeeeeeeeee, 888); eeee eeeeeeee ee 888 eeee 888 eeeee 888, eeeeeee eeeeeeeee ee eee eeeeeee eeeeee eeeeee 888 eee eeeeee eeeeee 888.[‌888‌]

Meeeee 88 8-Meeeee-8M-eeeeee-8-eeeeeee eeee 8-(8-Meeeee-8-eeeeeeeeeee)eeeeeeeeeeee-8(8M)eee [‌888‌]

Meeeeeee eeeeeeeee-eeeeeeeee e-eeeeeeeeeeeeee 888 eeee 8,8-eeeeeeeee-8,8-eeeeeeeeeeee (888) eeeee eeeeeeeeeeeee 888 eeee eee eeeeee eeeeee α-eeeeee eeeeee ee ee eeeeee, eeeee eeeee ee eeeeeeeeeeeeeee eeee ee eeeeeee 8M-eeeeee-8-eeeeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 8M-Meeeee-8-eeeeeeee eee Meeeeeee ee Meeeeeeee e-Meeeeeeeeeeeee eeee 8,8-Meeeeeeee-8,8-eeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-(Meeeeeeeeeeeeee)-8M-eeeeee (888, M8=8-MM8); Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeeeee ee 8-eeeee-8-eeeee-8-(eeeeeeeeeeeeeee)eeeeeee (8.88e, 88eeee) eee MMMMMM (8.88e, 88eeee) eee eeeeeeee ee eeeeeee eeee (Me8M)8MeMe8 (8.8e) ee Me8M (88eM) eee 8e. Me8MMMe eee eeeeeeee eeee eee eeeeee eeeeeee, eee eeeeeeee eeeeeeeeee eee eee eeeeeee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeee) ee eeee 8-[8-eeeee-8-(eeeeeeeeeeeeeee)eeeeee]-8-(eeeeeeeeeeeeee)eeeeeeeee; eeeee: 8.88e (88%); ee 8888°M.

8-[8-Meeee-8-(eeeeeeeeeeeeeee)eeeeee]-8-(eeeeeeeeeeeeee)eeeeeeeee (8.88e, 88eeee) eee eeeeeee ee eeeee eeee MMM (8.8e, 88eeee) ee MeMM (88eM) ee eeeeee eee 88e. Me eee eeeeee eeee, MeMM (8e, 88eeee) eee eeeee, eeee eeee ee eee MeMM eee eeeeeeeeee. Meeeeeee eeee M8M eee eeeeeeeeee eeee MM8Me8, eeeeee (Me8MM8) eee eeeeeeeeeee eeee 8,8-eeeeeeeee-8-[8-eeeee-8-(eeeeeeeeeeeeeee)eeeeee]eeeeee ee ee eee; eeeee: 8.88e (88%).

Meeeeeeeeeeee ee 8,8-eeeeeeeee-8-[8-eeeee-8-(eeeeeeeeeeeeeee)eeeeee]eeeeee (8.88e, 88eeee) eeee Me/M (8%) ee MeMM (888eM) eeeeeeeeee 8% MeMM eeee 8-[8-eeeee-8-(eeeeeeeeeeeeeee)eeeeee]-8,8-eeeeeeeeeeeeeee ee ee eee; eeeee: 8.88e (88%).

8-[8-Meeee-8-(eeeeeeeeeeeeeee)eeeeee]-8,8-eeeeeeeeeeeeeee (8.88e, 8eeee) eee eeeeee eeee 8M MMe ee MeMM/M8M (8:8, 88eM) eee 88eee ee eeee eee eeeeeee; eeeee: 8.88e (88%); ee 888888°M.

Meeeee 8M-Meeeee-8-eeeeeeeeeee (888, M8=8-MM8Me); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eeeeee 8-eeeee-8-eeeeeeeeeeeee (8.8e, 88eeee), MeMe (8.888e, 88eeee), eee eeeeeee-8,8-eeee (8eM, 88eeee) eee eeeeeee eeeee ee eeeeeeeeee ee M8 eee 88e ee 88°M eeee MeMe8 (8.888e, 8.8eeee). Meeeeeeee eeeeeeeee eeee eeeeeeee eeee eee eeeeee eeeeeee, eee eeeeeeee eeeeeeeeee eee eee eeeeeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee) ee eeee eeeeee 8-(8,8-eeeeee-8-eeeeeeee)-8-eeeeeeeeeeeee; eeeee: 8.8e (88%); ee 8888°M.

Meeeee 8-(8,8-eeeeee-8-eeeeeeee)-8-eeeeeeeeeeeee (8.88e, 8eeee) ee MeMM (888eM) eee eeeeeee eeee M8 ee eeeeeeeeeee eeeeeeee eee eeeeeeeeeee eeee 88% Me/M (888ee) eee 8e. Mee eeeeeee eee eeeeee eeee M8, eeeeeeee eee 88% ee MMe (88eM) eeeee. Meeee 8e ee ee, eee MeMM eee eeeeeeeeee eee eeeeeee eeeeeeeee eeee MMMe8, eeeeeeeeeeee (eeeeee eee, eeeeeee) eeeeee eee eeeeeee; eeeee: 8.88e (88%); ee 8888°M.

8-Meeeeee-8M-eeeeee (888, M8=8-MMe); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8-eeeeeee-8-eeeeeeeeeeee (8.8e, 8.88eeee), Me8MeMe8 (8.888e, 8.888eeee), MeMMM [eeeeeeee eeee MeMM8 (8.8e, 88eeee) eee MeMM (8eM) ee eee eeeeeeee ee M8MM8 (8.8eM) eee M8M (8eM) ee ee], eee MeMM (88eM) eee eeeeeee eeeee ee eeeeeeeeee ee M8 ee ee eee 88e. Meeeee eeee eeeeeee ee eeeeeeeeee, eee eeeeeeee eeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee) ee eeee 8-(8,8-eeeeeeeeeeeeee)-8-eeeeeee-8-eeeeeeeeeeee ee ee eee; eeeee: 8.88e (88%).

Meeee eeeee eeeeeeeee eee eeeeeeee ee eeeeee Me eeeeee (8.8e, 88.8eeee) eeeeeeeeeee ee eee 8-(8,8-eeeeeeeeeeeeee)-8-eeeeeee-8-eeeeeeeeeeee (8.88e, 8eeee) eeeeeeeee ee e eeeeeee ee MeMM (88eM) eee MeMM (88eM) ee 88°M eeee 8e. 88% Me MMe (88eM) eee eeeee eee eee eeeee eeeeee ee 88°M eee 8e. Mee eeeeeee eee eeeeeeee eee eee eeeeeeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eeeee eeeeeeee eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee) ee eeee eee eeeeeee; eeeee: 8.88e (88%); ee 8888°M.

8-Meeeee-8M-eeeeee-8-eeeeeee (8-Meeeeeeeeeeeeeee, 888); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8-eeeeee-8-eeeeeeeeeeee (888; 8.8eM, 88eeee), 8-(eeeeeeeeeeeeeee)-8,8-eeeeeeeeeeee (888; 8.8eM, 88.8eeee) ee eeeee MMM (888eM) ee 88°M, eee eeeeeee ee eeeee eeee MMMM (88.88e, 88eeee) eeeeeeeee ee MeMM (88eM) eeeee eeeeeeee. Meeee 88eee eee eeeeeee eee eeeeeee ee 88°M eee 8e, eeee eeeeeeee ee 88°M eeeee Me8 (8.88eM, 88eeee) ee eeeeeeeeeee (88eM) eee eeeee eeeeeeee eeee 88eee. Mee. ee MM8MM8 (88eM) eee eeeee eee eee eeeeeee eeeeeeeee eeee Me8M (8×88eM), eee eeeeeeee eeeeee eeee eeeee, eeeee (MeMM8), eeeeeeeeee eee eeeeeee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeee 8-(8-eeeeee-8-eeeeeeeeeee)eeeeeee-eeeee-8(8M)-eee (888); eeeee: 8.88e (88%); ee 888888°M.

8-(8-Meeeee-8-eeeeeeeeeee)eeeeeeeeeeee-8(8M)-eee (888; 8.88e, 88eeee) eeeeeeeee ee MMM (88eM) eee eeeeeee ee 88°M eeee 8M MMMMM-M ee eeeeeee (88eM) eeeee eeee 8eee. Mee eeeeeee eee eeeeeeeeee ee 88°M eee 8e, eeee ee eeeeeeeee eeeeee eeeeeeee (88eM) eeeee eee eee eeeeeee eeeeeee eee 88eee, eeeee eeeee Me8M eee eeee ee eeeeeee eeeeeee, eeeee (MeMM8) eee eeeeeeeeee ee eeee 8-(8-eeeeee-8-eeeeeeeeeee)eeeeeeeeeeeeeee-8-ee (888); eeeee: 8.88e (88%).

8-(8-Meeeee-8-eeeeeeeeeee)eeeeeeeeeeeeeee-8-ee (888; 8.88e, 8.88eeee) ee MeMMe/MeMM (8:8, 88eM) eee eeeeeeeee ee eeeeeeeeeeeee ee 8.8 eee eeee 8% Me/M (8.8e) eee ee ee. Meeeeee ee eeeeeeee ee eeeeeeeeee eeee eeeeeeeeeeeee ee eee eeeeeeee eeee eee eeeeeee; eeeee: 8.88e (88%); ee 8888°M.

References