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10.13.1.1.1.4.1.1.6 Variation 6: From 2-(o-Nitroaryl)enamines; Leimgruber–Batcho Synthesis

DOI: 10.1055/sos-SD-110-00001

Joule, J. A.Science of Synthesis Knowledge Updates, (20102108.

The Leimgruber–Batcho synthesis (Scheme 146, see Table 6 for examples), like the Reissert approach, depends on the acidity of methyl groups ortho to aromatic nitro groups. The first step involves condensation of a 1-methyl-2-nitroarene 437 with hot dimethylformamide dimethyl acetal (DMFDMA) (no added base being necessary) and leads to an enamine 438, which is normally isolated. Subsequent reduction of the nitro group, in neutral or acidic conditions, then leads directly to the 2,3-unsubstituted indole 439.[‌370‌,‌371‌] Each step is operationally straightforward.

Meeeee 888 Mee Meeeeeeeee–Meeeee Meeeee Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeeeeee (Meeeee 888 eeeee eee eeeeeeee eeeee MMMMMM) eeee eeeeeee ee eeeeeeee ee eeeeeee eeeeeeeeee ee eee eeeeeeeeeeeeeeeee eeeeeeee eeeeee eeeeeeeee eeeeeeeee (eeeee eeeeeeeeeeee eee eeeeeeee eeeeee ee 888 eeeeee 888) eee ee eeeeeeeeeeeee eeeeeee, MeMMM=M+Me8, eeeee eeeeeeee eeee eee eeeeeeeeeeee eeeeeeee eeeeeeeee eeeeeeeee 888, eeee ee eeeeeeee ee 888 eeeee eee eeeee eeee, eee eee eeeeeee eeee eee eeeeee eee ee eeee eee eeeee ee eeeee eee eeeeeeee ee eeeeeeeeee ee eeeeeeeee eeeee. Meeee eeeee eeeeeeeee ee 888 eee β-eeeeeeeeeee ee eee eeeeeeee eeeeeee eeeeeeeee 888, eeeeeeeeeeeeee eeeee-ee-eeeeeee eeeeeeee eeeeeee 888 eee e eeeee eeee ee eeeeeeeeeeeee eeeeee eee eeeeee 888.

Meeeee 888 Meeeeeeee ee eee Meeeeeeeee–Meeeee Meeeeeeee[‌888‌,‌888‌]

Mee eeeeeeeeeeeeeeeee eeeeeeee eeeeee eeeee ee eeeeeee eeeeeeeee ee 888–888°M, eeeeeee eeee-eeeeeeeee(eeeeeeeeeeeee)eeeeeee ee eeee ee eeeeeeee eeeeee eee ee eeee ee 88–88°M,[‌888‌] eeee(8-eeeeeeeee)eeeeeee[‌888‌,‌888‌] ee eeee eeeeeeeee eee ee eeee ee 888–888°M, eee eee eee ee eeee(eeeeeeeeeeeee)eeeeeee[‌888‌] eeee eeeeee eee eeeeeeee ee ee eeeeeeeee ee eeeeee 888–888°M. Mee eeeeeeeee ee eeeeeeeeeee ee eeeeeeeeeeee ee eeeeeeeeeeee eee eeeeeeeeeeee; eee eeeeeee ee eeee e eeeeeeeeee-8-ee eeeeeee.[‌888‌‌888‌] Meee eeeeeeeeeeee eeeee eeeeeeee eeee eeeeeeeee eeeeeee.[‌888‌]

Meeeeee eeeeeeeeee eee eeee eee eee eeeeee eeeee ee eee eeeeeeeee eeeeeeeee eeeeeeeee eeeeeeeee eeee eeeeeeeee[‌888‌] ee eeeeee[‌888‌] (eeee eeeeeeee ee eeee eeeeeeeee[‌888‌]), ee eeeeeeee eeeeeeeeee eeee ee eeee/eeeeee eeee,[‌888‌] eeee(MM) eeeeeeeee ee eeeeeee eeeeeee, eee(MM) eeeeeeee ee eeeeeeeeeeee eeeeeeeeeeee eeee,[‌888‌] eeeeee eeeeeeeeee, eeeeee eeeeee,[‌888‌] eeee/eeeeee eee/eeeeee eeee,[‌888‌] eee eeeeeee eeeeeeee(MMM) eeeeeeee.[‌888‌,‌888‌]

Mee eeeeeeeeee ee eeeeeee eeee eeeeeeeeeeee eeee eeee eeeeeeee eeeeeeeee eee eeeeeeeeeeee. Mee ee eee eeee eeeeeeee eeee eee eeee eee eeeeeeeeeeee ee eeee eeeeeee eeeee eeeeeeee ee eeeeeeeee ee eeeeeeeeeeeee,[‌888‌,‌888‌] ee eee eeeeeeee ee e eeeeeeeeeeeeeeeeeeeeee; eee eeeeeeee eeeeeee 8,8-eeeeeeee-8,8-eeeeeeeeeeeeee (888) ee eeeee ee Meeeee 888, eeeeeee eeeeeeeee ee eee eee-eeeeeee 888 eeeee 8,8-eeeeeeeeeeeeee[8,8-e]eeeeee (888).

Meeeee 888 8,8-Meeeeeeeeeeeee[8,8-e]eeeeee eeee “Meeeee” Meeeeeeeee–Meeeee Meeeeeeee[‌888‌,‌888‌]

Meeeeee eeeeeee eee ee eee eeeee eeeeeeee eeeeeeeeeee 888 (Meeeee 888); eeee, eee eeeeeee eeeeeeeeeeee 888 ee eeeeeeeeee, eee eeeeeeee 888 eeee eeeeeeee ee eeeeeeeee eeee eeeeee eeeeeeeeeeee eeeeee 888, eee eeee, ee eeeeeeeee, eeeeeeeeeee 888 eee eeeeeeee.[‌888‌]

Meeeee 888 Meeeeeeeeee eeee Meeeeeeeee–Meeeee Meeeeeeee[‌888‌]

Meeee eee eeeeeeeeee eee eeeeeeee ee eeeee eee eeeee eeee eeeeeeee eeeeeeeeeeee eeee ee eeeee eeeee eeeee eeee e eeeeee eeeee: 8-eeeee-8-eeeeeeeeeeee eee eeee eeeeeeeee eeeeeee ee 8-eeeeee-8M-eeeeee,[‌888‌] eee 8-eeeee-8,8,8,8-eeeeeeeeeeeeeeeeeeeeee, e.e. 888, eee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeee eeeeeee 888 eee eeeeeeee 888 (Meeeee 888), ee eeee ee eeeee eeeee eeeee eeee-eeeeeeeee(eeeeeeeeeeeee)eeeeeee ee eee eeeeeeeeee eeeeeee.[‌888‌]

Meeeee 888 Meeeeeeeee–Meeeee Meeeeeeee Meeeeeeee Meeeeeeee e-Meeee Meeeeeeeeeee[‌888‌]

Meeee 8 Meeeeee eeee Meeeeeeeee–Meeeee Meeeeeeee[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌‌888‌]

Meeeeeee Meeeeeee Meeeeeeeee M Meeeeeeeee MM Meeeeee(e) Meeee (%) Mee
eeeeee
8-eeeeee-
8-eeeeeeeeeeeee
MM(MMe)8MMe8,
MMM, 888°M
M8, Me/M,
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8-eeeeeee-
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8-eeeeeeeeeeee
MM(MMe)8MMe8,
MMM, eeeeeeeeeee,
888°M
M8, Me/M,
MeMMe
88 [‌888‌]
8,8-eeeeeeee-
8,8-eeeeeeeeeeeeee
MM(MMe)8MMe8,
MMM, 888°M
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MeMMe
88 [‌888‌]
eeeeee
8-eeeeee-
8-eeeeeeeeeeeee
MM(MMe)8MMe8,
MMM, eeeeee
MeMe8, M8M 88 + 88 [‌888‌]
8-eeeeeeeee
-8-eeeeee-
8-eeeeeeeeeeee
MM(MMe)8MMe8,
MMM, eeeeeeeeeee,
888°M
Meeee Me,
M8M8, 88°M
88 [‌888‌]
8-eeeeeeeee-
8-eeeeee-
8-eeeeeeeeeeee
(8-eeeeeeeee)8MM8,
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MeM8, MeMM,
M8M8
88 [‌888‌]
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8-eeeeee-
8-eeeeeeeeeeee
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888°M
Me, M8M,
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88 [‌888‌]
8-eeeee-
8-eeeeee-
8-eeeeeeeeeeee
MM(MMe)8MMe8,
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Me, M8M,
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88 [‌888‌]
8-eeeee-
8-eeeeee-
8-eeeeeeeeeeee
MM(MMe)8MMe8,
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Me, M8M,
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88 [‌888‌]
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8-eeeeee-
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88 [‌888‌]
8-eeeeee-
8-eeeeeeeeeeee
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MM(MMe)8MMe8,
MMM, 888°M,
eeee MMMMe,
MeMM, eeeeee
M8, Me/M,
MeMM eeee
8-eeeeeeeeeeeeeee-
8-eee, MeMM, Me8MM8,
eeee MeM(MMe)8M
88 [‌888‌]
8-(eeeeeeeeeeeee)-
8-eeeeee-8-
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MM(MMe)8MMe8,
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888°M
Meeee Me,
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88 [‌888‌]
8-eeeee-
8-eeeeeee-8-
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MM(MMe)8MMe8,
MMM, eeeeeeeeeee,
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Me, MeMM,
88°M
88 [‌888‌]
8-eeeeee-
8-eeeeeeeeeeeeee
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88 [‌888‌]

Me eeee eeeee, eee eeeeeee eeeeeeeeeeee ee eeeeeeeee eeee e 8-(e-eeeeeeeee)eeeeeeeeeeee eeeeeeeeeeeee eeeeee eeeeeeeee eeeeeeeeeee.[‌888‌,‌888‌] Me eeeeee, ee ee eeeeeeeee eeee ee eeeeee ee e 8-(e-eeeeeeeee)eeeeeeeeeeee; eeee eeee eeeeeeeee ee eeeeeeee eeee eeeeeeeee eeeeeeeee ee eee eeeee eeeee ee eeeee eeeeeeeeeeee ee eeeee eeeeeeeeeeee eeee eee eeeeeeee ee eeeeeeee eeeeee eeee eeeeeee ee 8-eeeee-8M-eeeeeee.[‌888‌]

Meeeeeeeeeeee eeeeeeeeee ee eee eeeeeeeee-eeeeeee ee eee Meeeeeeeee–Meeeee eeeeeeee eee ee eeeeeeee ee eeeeeeeeeee eeeee, e.e. eee eeeeeeee ee ee e-eeeeeeeeeeeeee 888 eeee 8-eeeeeeeeeeeeeee-8-eee (888) (Meeeee 888) ee 8-(8-eeeeeeeeeee)eeeeeeeeee ee eee eeeeeeee ee eeeeeeeee(MM) eeeeeee eeeee eeeeeee eeeeeeeeeeeee 888 ee eee Meeeeee­eee–Meeeee-eeee eee eeee eeee eeeeeeeee eeeee eeeeeee, e.e. 8-eeeee-8M-eeeeee (888).[‌888‌] 8-(e-Meeeeeeee)-8-eeeeeeeeeeeeeeee (eeee-eeeeeeeeeeeeee eeeeeeeee), e.e. 8-(e-eeeeeeeee)eeeeeeeeeeeeee eeeeee, eeeeeeee eee Meee eeeeeeee, eeeee eeee eeeeee ee 8M-eeeeee-8-eeeeeeeeeeee ee eeeeeee ee eeeeee eeeeeeeee.[‌888‌]

Meeeee 888 8-Meeee-8M-eeeeee eee Meeeeeee ee ee e-Meeeeeeeeeeeee eeee 8-Meeeeeeeeeeeeee-8-eee[‌888‌]

Meeeeeeeeeee Meeeeeeee

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

Meeeeeeeeeeeeeeeeeee (8.88 e, 88.8 eeee) eee 8-(eeeeeeeee)-8-eeeeee-8-eeeeeeeeeeee (8.88 e, 88.8 eee) eeee eeeee ee 888°M eee eeeeeee eeeee ee eeeeeeeee eeeeee eee 8 e. Mee eeeeeee eee eeeeee eee eee MeMM (888 eM) eee eeeee. Mee 8-{8-[8-(eeeeeeeee)-8-eeeee­eeeeee]eeeee}eeeeeeeeee eeeeeeeeeeee ee eeeeee eee eeeeee; eeeee: 8.88 e (88%); ee 88–88°M.

Mee 8-{8-[8-(eeeeeeeee)-8-eeeeeeeeeee]eeeee}eeeeeeeeee (8.88 e, 88.8 eeee) eee eeeee ee e eeeeeee eeeeeeeeee ee eeeeee eeeeee [eeeeeeee eeee eeeeee eeeeeee (88 eeee)] ee eee MeMM (888 eM) eee eee eeeeeee eee eeeeee ee eeeeee. Meeeeeeee eeeeeee (8.8 e, 88 eeee) ee eee MeMM (88 eM) eee eeeee eeeeeeee eeee 88 eee, eeeeee eeeee eeee eeeeeeee eeeeeeeee ee eee eeeeeeee. Meeee eeeeeee, eee eeeeeee eee eeeeeeee eeeeeee e eee ee Meeeee eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeee eeee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/eeeeeeeeeee 8:8) ee eeeeee eee eeeeeee ee e eeeee eeeee; eeeee: 8.88 e (88%); ee 88–88°M.

M eeeeeee eeeeeeeee eee eeee eeeeeeee ee eeeeeeeee ee eee[‌888‌].

Meeeee 8-(8-Meeeee-8-eeeeeeeee)-8M-eeeeee-8-eeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

8-Meeeee-8-eeeeeeeeeeee eeee (8.88 e, 88 eeee) ee e eeeeeee ee MM(MMe)8MMe8 (8.888 e, 88 eeee) eee MMM (88 eM) eee eeeeee ee 888°M eeeee M8 eee 88 e. Meeeeeeeeeeee eeeee eeeeeee eeeeeeee eeee e eeeeee eee, eeeee eeee eeeeeeee ee eeeeee 8-[8-(eeeeeeeeeeeee)eeeee]-8-eeeeeeeeeeeee eeee MeMM (88 eM) ee 8°M; eeeee: 8.88 e (88%); ee 88–88°M.

Meeeee 8-[8-(eeeeeeeeeeeee)eeeee]-8-eeeeeeeeeeeee (8.8 e, 88 eeee) eeeeeeeee ee MeMM (888 eM) eee eeeeeee eeee MMMMe (8.8 e, 88 eeee) ee eeeeee eee 88 e. Meeeeeeeeee ee eee eeeeeeee eeeeeeee eeeee eeeeeee eeeeeeee eee eeeeeeee ee eee eeeeeeee ee MeMMe eee eee. ee MeMMM8. Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeee eeee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee ee eeee eeeeee 8-(8,8-eeeeeeeeeeeeee)-8-eeeeeeeeeeeee ee e eeeeee eee, eeeee eee eeeeeeeeeeee (Me8M); eeeee: 8.88 e (88%); ee 88–88°M.

Meeeeeeee ee eee eeeee eeeee ee eeeeee 8-(8,8-eeeeeeeeeeeeee)-8-eeeeeeeeeeeee (8.88 e) eee eeeeeeee eeeee eeeeeeee ee 8.8 eee eeee 88% Me/M (8.8 e) ee MeMM eeee. Mee eeeeeeee eee eeeeeee ee eeeeeeeeee eeeeeee Meeeee, eee eee eeeeeeee eee eeeeeeeeeeee ee eeee e eeeee eeeee, eeeee eee eeeeeeeeeeeeee (Me8M/eeeeee) ee eeee eeeeee 8-eeeee-8-(8,8-eeeeeeeeeeeeee)eeeeeeee; eeeee: 8.8 e (88%); ee 88–88°M.

Meeeee 8-eeeee-8-(8,8-eeeeeeeeeeeeee)eeeeeeee (8.88 e, 8.8 eeee) eee 8-eeeeeeeeeeeeeee-8-eee (8.88 e, 88 eeee) ee MeMM (88 eM) eeee eeeeeee ee eeeee Me8MM8 (8.8 e, 88 eeee) eee 88 eee ee ee, eee eeee MeMM(MMe)8 (8.88 e, 88 eeee) eee eeeee ee eeeeeeee eeee 8 eee. Meeee e eeeeeee 88 eee ee ee, eee eeeeeee eee eeeeee eeee ee MeMMM8 (88 eM) eee eee eeeee eee eeeeeeeee eeee MeMMe/eeeeee (8:8). Mee eeeeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeee ee eeeeee ee MeMM eeee 8 M MMe eee 8 e eee eeee eeeeeeeeeeee ee eeee eee eeeeeeeeeeeee ee eeeeee 8-(8-eeeeee-8-eeeeeeeee)-8M-eeeeee-8-eeeeeeeeeee; eeeee: 8.88 e (888%); ee 888–888°M (eee).

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

Mee eeeeeeee ee 8-eeeeeeeeeeeeeee-8-eee (888; 8.88 e, 88.8 eeee) eeee 8-eeeee-8-eeeeeeeeeeee (888; 8.88 e, 88 eeee) eee eeeeeeee ee eeeeeee ee e eeeeee eeee ee 888°M eeee Me(MMe)8 (8.888 e, 8.888 eeee), eeee(8-eeeee)eeeeeeeee (8.888 e, 8.88 eeee), eee Me8M (8.88 e, 88.8 eeee) ee MeMM (88 eM) eee 88 e. Mee eeeeee eeeeeee eee eeeeeeeee eeee eeeeeeeee eeeee, eeeeeeeeeeee, eee eeee eeeeeee eeee 88% ee MMe (88 eM) ee MeMM (88 eM) ee ee eee 88 e. Mee MeMM eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeeeee ee eee eeeeeeee ee MeMMM8. Mee eeeeeee eee eeeeeeeee eeee Me8M, eee eee eeeeeeee eeee eeeeee eeee eeee M8M, eeeee (MeMM8), eee eeeeeeeeeeee. Meeeeeeeeeeeee [eeeeee eee, eeeeee/eeeeeee (MMMMMMM:eeeeeeeeee) 8:8], eeee eee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.

References


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