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Please login or sign up for a free trial to access the full content. Method 1: From 2-(Arylamino)aldehydes, α-(Arylamino) Ketones, or Synthons Thereof

DOI: 10.1055/sos-SD-110-00001

Joule, J. A.Science of Synthesis Knowledge Updates, (20102182.

In early examples of this type of approach, arylamines 674 were alkylated with 4-halo-substituted acetoacetic esters and the products 675 ring closed using zinc(II) chloride to give ethyl 1H-indole-3-acetates 676 (Scheme 247).[‌622‌]

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8-Meeeeeeeeee eee ee eeeeeeeee ee eeeeeeeeee Meeee eeee eeeeeeeee eeeeeee ee M-eeee­eeee­eeeeeeeeee; Meeeee 888 eeeee eee eeeeeeeee ee eee eeee-eeeeeee eeeeeeeee 888 eeee 888, eeeeeeeeee eeeeeeeee 8-(8-eeeeeeeeeeee)-8-eeeeee-8M-eeeeee (888).[‌888‌,‌888‌] Meeeeeee eeeeeeeeeee ee eeee ee ee eeeeee (eeeee eeee eee eee eeeeeeeee ee 8-eeeeee-8M-eeeeee 888 eeeeee eeee e 8-eeee-8M-eeeeee)[‌888‌] eeee eeee(MM) eeeeeeee, eee, ee eee eeee, eeeeeeeeeeee eeee eee ee eeeeeee ee eeee eeeeeeeeeee ee eeeeeeeeeeeee ee eee eeee eeeee ee eee 8-eeeeeeee eeeeee.[‌888‌,‌888‌]

Meeeee 888 8-(8-Meeeeeeeeeee)-8-eeeeee-8M-eeeeee eeee ee M-Meeeeeeeeeeeeeeee eee 8-Meeee-8-eeeeee-8M-eeeeee eeee ee M-Meeeeeeeeeeee[‌888‌‌888‌]

M-Meeeeeee α-eeeeeeeee eeeeeee eee ee eeeeeeee eeeee eeeeeeeeee eeee eeeeeeeeee eeee eeeee eeeeeeee ee eee eeeeeeeee Meeeeeee eeeeeee (eee Meeeeee, eeee eeeeeeee ee eeeeeee eee ee eeee ee eeeeeee eeeeeeeeeeee eeee eeeeeeeeeeeee eeeeeee. Meeeee 888 eeeee eeeeeeeeeeeeeeeeee eeeeeee 888 eeeee eeeeeeeee eeee eeeeeeeeeeee eeee eeeeeeeeeeeee eeeeeee 888.[‌888‌,‌888‌,‌888‌] Meeeeeeeeeeeeeeee eeeeeee eee ee eeeeee eeee eeeeeeee(MM) eeeeeeee[‌888‌,‌888‌] eee ee M-eeeeeeeeeeeeeeeee eeeeee eee ee eeeeeeeee eeeee eeeeeeeeeeeeeee eeee ee eeee eeeeeeeeeee.[‌888‌]

Meeeee 888 8-(Meeeeeeeeeeeeee)-8M-eeeeeee eeee 8-[Meee(eeeeeeeeeeeeeee)eeeee]eeeeeeeeeeee Meeeeee Meeeeee[‌888‌,‌888‌,‌888‌]

Mee eee eeeeeeeee eeeeeee eeee ee 8,8-eeeeeeeeeeeeeeee, eeeeeeeeee eeee eeeee eeeeeee ee eee eeeeeeee ee eeeeeee eeeeeee eee eeeeee eeeeeeee eeeeeeeee ee eeeeeeeeee ee eeee eeeee eeeee eee eeee eeeeeee.[‌888‌]

Meeeeeeee eeee eee M—M eeee ee eeeeeeee ee eeeeeee- ee, eeeeee, eeeeee-eeeeeeeee eeeeeeee ee 8-eeeee-8,8-eee eeeeee eeeeeeee 8-(eeeeeeeee)-8,8-eee eeeeee eee eeeee eee ee eeee eeeeee ee eeee 8M-eeeeee-8-eeeeeeeeeeee, e.e. 888, eeeee Meeeeeeee 88 ee eeeee eeeeeeeeeee–eeeeeee eeeee eeeeeee ee eee eeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeee ee Meeeee-Meeeeeeee Meeeeeeee eeee eee M—M Meee ee Meeeeeee[‌888‌]

Meeeeeee eeee ee 888, eeeeeeeee ee eeeeeeee ee (eeeeeeeee)eeeeeeee ee 8-eeeeeeeee eeeeeee 888 eeee eeeeeeeeeeeeeeeee eeeeeeee eeeeee, eee eeeeeeee eee 8-(eeeeeeeee)eeeeeeeee. Meeee eeeeeeeeee eee ee eeeeeeeee eeee 8M-eeeeeee 888 eeeee Meeeeee–Meeeee eeee eeeeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 8M-Meeeeee eeee Meeeeeeeee[‌888‌]

Meeeeeeeeee 888

M8 M8 Meeee (%) Mee
M MMe 88 [‌888‌]
Me MMe 88 [‌888‌]
Me MMe 88 [‌888‌]
Me Me 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeee 8-Meeeee-8M-eeeeee-8-eeeeeee (888, M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

M-Meeeeeeeeeeee (88.8 e, 8.8 eee) eee eeeee 8-eeeee-8-eeeeeeeeeeee (88.8 e, 8.8 eee) eeee eeeeeee ee eeeeeee eeee (MMMMMMM: eeeeeeeeee) ee ee eeeeeeeee. M eeeeeeeeeee ee M-eeeeeeeeeeeee eeeeeeeeeeee eeeeee eee eee eeeeeeee eee. Mee eeeeeee eeee eee eeee eeeeeeeee eeee 8 M ee MMe eee eee eeeeeee eeeee eee eeeeeeee eee eeeeeeeee eeee eeeeeee. Mee eeeeeee eeeeeee eee eeeeee, eeeee, eee eeeeeeeeeeee ee ee eeeee eeeeeee eeeeeeee ee eeee eeeee 8-(eeeeeeeeeeeee)-8-eeeeeeeeeeee; eeeee: 88 e (88%), eeeee eee eeeeeeee eeeeeee eeeeeee eeeeeeeeeeee.

M eeeeeee ee eeeee 8-(eeeeeeeeeeeee)-8-eeeeeeeeeeee (88 e, 88 eeee) eee eeeeeeee MeMe8 (88 e) eee eeeeee eee 88 eee eeeee e eeeeee ee M8 eeee eee eeeeeeeeeee eeee ee 888°M. Meeee e eeeeeee 88 eee ee 888°M, eee eeeeeee eee eeeeee eee eeeeeeeeeee eeeeeee Me8M eee 8 M ee MMe. Mee Me8M eeeee eee eeeeee, eeeee, eee eeeeeeeeeeee ee eeee eeeee eeeeeeee (8.8 e), eeeee eee eeeeeeeee ee 888–888°M/8 Meee ee eeee eee eeeeeee; eeeee: 8.8 e (88%); ee 888°M.

8-Meeee-8-eeeeee-8M-eeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeee eeeeeeeeeee eeee ee e eeeeee eeeeeeee ee eee eeeeeee eee eeeeee eeeeeeeee eeee eeeee.

8-(M-Meeeeeeeeeee)eeeeeee (8.88 e, 8.88 eee) eee MeMe8 (8.88 e, 8.88 eee) eeee eeeeee eeeeeeee ee 888°M eee 8 e. Meeeee eeeeee eeeeeeee eee eeeeeee; eeeee: 8.88 e (888%).

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

Me e eeeeeee ee MMMM (88 eM) eee MMM (88 eM) ee eeeeee eeeee M8 eee eeeee M-(8,8-eeeee­eee­eeeee)-M-(eeeeeeeeeeeeeee)eeeeeee (8.8 e, 88 eeee) eee eee eeeeeee eee eeeeee ee eeeeee eee 88 e. Mee eeeeeeee eeee eeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee ee eeee eee eeeeeee; eeeee: 8.88 e (88%); ee 88–88°M.

Meeeee 8-Meeee-8,8-eeeeeeee-8M-eeeeee-8-eeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

Me eeeeee 8-eeeee-8-eeeeeeeeeeee (88 ee, 8.888 eeee) eee 8-eeeee-M-eeeeeeeeeeeee (888 ee, 8.888 eeee) ee eeeeeee (88 eM) eee eeeee eeeeee(MM) eeeeeeeeeeeeeeee eeeeeee (8 eee%). Mee eeeeeee eee eeeeee ee eeeeee eee 8 e. Meeeeeeee 88 (888 ee) eee eeeee, eee eee eeeeeee eee eeeeee ee eeeeee eeeeeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee) ee eeee eee 8M-eeeeee ee e eeeeeeeee eeeee; eeeee: 888 ee (88%); ee 88–88°M.