Science of Synthesis

Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 340.

Indolyl anions will add in Michael fashion to acrylonitrile[‌1442‌,‌1443‌] and methyl acrylate[‌1444‌] (see also ‌Table 34‌), in each case using phase-transfer methodology. Addition of 1H-indole through nitrogen to 4-vinylpyridine has been reported, though under strenuous conditions.[‌1445‌]

M-Meeeeeeeee ee eeeeeee eee eeeeeee eeeee-8-eeeeeeeee,[‌888‌] eeeeeeeee eeeeeeeeeeeeee ee eeeeeeee eeee eeeeee eeeeeee (eee eeeeeee, 8-{[8-(eeeeeeeeeeeeee)eeeeee]eeeeee}-8M-eeeeee (‌8888‌, ‌Meeeee 888‌),[‌8888‌] 8-(eeeee-8-eeeeeeeee)eeeeeeeeeeeeeeee[‌8888‌] eee 8-(8,8-ee­eeee­eeeeeeeeeeeeeeeeeeee)-8M-eeeeee[‌8888‌] eee eeee ee eeee eee), ee eeeee-8-eeeeeeeeeeee eeeeeeeee eeeee eeeeeeeee eeee-eeeeeeee ee e eeeeeee eeeeeee eeeeeee[‌88‌] ee eeeeeeee eeeeeeeee/eeeeee eeeeeeeee ee eeeeeee[‌888‌] ee eeeeeeee eeeeeeeee[‌8888‌] [8-eeeeee-8M-eeeeee[‌8888‌] (‌8888‌, ‌Meeeee 888‌) eee 8-(eeeeeeeeeeee-8-eeeeeeee)-8M-eeeeee eee eeee[‌8888‌] ee eeee eee] ee eeeeeeeeeeeeeeeee,[‌8888‌] ee eeee eeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeee eeeeeee[‌8888‌] ee ee ee eeeee eeeeee, 8-eeeee-8-eeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeee ([eeee]MM8).[‌8888‌] Meeeee eeeeeeeee eeee 8,8-eeeeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeee-8(8M)-eee ee 88°M ee eeeeeeeee eee M-eeeeeeeeee eeee eeeeeeee ee eeeee eeeeeee[‌8888‌] eee eeeeee eeeeeeee ee Meeeee ee eeeeeeeee eeeeeeeeeeee eee ee eeee eee M-eeeeeeeeeee.[‌8888‌] M-Meeeeeeeeeeeeeeeee ee eeeeeee eee ee eeeeeeee eeee eeeeeeeeeeeeeeeeee eeee eeeee eeeeee eeeeeeeeeeeeeeeeeeeeee ee eee eeee eeee 8-(eeeeeeeeeeeee)eeeeeeee, eeeeee(MM) eeeeeee, eee eeeeee eeeeeeeeeeee eeeeeee.[‌8888‌]

‌Meeeee 888‌ Meeeeeeee ee 8-{[8-(Meeeeeeeeeeeee)eeeeee]eeeeee}-8M-eeeeee eee eee Meeeeee Meeee[‌8888‌]

‌Meeeee 888‌ Meeeeeeee ee 8-Meeeee-8M-eeeeee eee eee Meeeeee Meeee[‌8888‌]

Mee eeeeee eeeee ee ee eee eeeeee eeeee-eeeeeeee eeeeeeeeeee[‌888‌–‌888‌,‌888‌] [8-eeeeee-8M-eeeeee (‌8888‌, ‌Meeeee 888‌), 8-(8-eeeeeeeeeee)-8M-eeeeee,[‌8888‌] eee 8-eeeee-8M-eeeeee (‌8888‌, ‌Meeeee 888‌) eee eeee ee eeee eee] ee ee eeeeeee eeeee-8-eeeeeeeeee[‌8888‌] eeeeeeeee ee eeeeeeee eeee eeeeeeeeeeee [8-(8-eeeeeeeeeee)-8M-eeeeee (‌8888‌, ‌Meeeee 888‌) ee eeee ee eeee eee]. Meeee eeeeeee eeee eeeeeeeee eee eeeeeeee eee eeee eeeeeeeeee eee ee eeeeee eeeee ee eeeeee eeeeeee.[‌888‌]

‌Meeeee 888‌ Meeeeeeee ee 8-Meeeee-8M-eeeeee eee eee Meeeeee Meeee[‌888‌]

‌Meeeee 888‌ Meeeeeeee ee 8-Meeee-8M-eeeeee eee eee Meeeeee Meeee[‌888‌]

‌Meeeee 888‌ 8-(8-Meeeeeeeeee)-8M-eeeeee eee eee Meeeeee Meeee[‌8888‌]

Meeeeeee eee eeeeeeeeeee eeee ee eeeeee ee eeeee-8-eeeeeeeeee ee ee eee eeeeeeee, eeeee eee eeeeeeeeeee eeeeeeee ee eeeee eeeeeeee ee M8;[‌8888‌] eee eeeeeee, eeee 8-eeeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeee ee M8 eeeeee eeeeee eeeeeeeeee eeeeeeeeeee.[‌8888‌] Meee eeeeeee eee eeeeeeeee eeeeee[‌88‌,‌888‌,‌8888‌] eee eeeeeeee ee eeeeee M-eeeeeeeeeee; eee eee ee eee eeeeee eeeeeee eee eeeeeeeeee ee eeeeeeeee eeeeeeeeee ee M8 (‌Meeee 88‌). Meeeeee eeeeeee, ee ee eeeee ee MM8 eeeeeeeee, eeee eeeeee eeee eeeeeeeee eeeeeee. Meeeeeee eeeee ee M-eeeeeeeeee eeeeee eeeeee eeee eeeeeeeee eeeeee eeeeee eeeeee eeeee ‌8888‌ (‌Meeeee 888‌).[‌888‌,‌8888‌,‌8888‌] Meeeee M-eeeeeeeeeee eee ee eeeeeeee eeee eeeeeeee eeeeeeeee;[‌8888‌] ee ee eeeeeeee eeee eee eeee eeee ee 8,8-eeeeeeeeeeee[8.8.8]eeeeee, eeeee eeee eeeeee ee eee eeee: ee e eeeeeeeeeeee eeeeeeee eee ee eeeeeeeeeee eee eeeeee (eeeee eeeeeee eeeee eee eeee ee M-eeeeeeeeeeeeeeeeeeee eeeeeee). Meee 8M-eeeeee-8-eeeeeeeeee eeee eee ee M-eeeeeeeeee ee 88% eeeee ee eeee eeeeee, ee eeee eeeeee 8-eeeeee-8M-eeeeee-8-eeeeeeeeeee.

Me eee eeeeeeee ee eeeeeeeeeee eeeeee eeeeeeeee, eeeeeee eeeeeeeeee eee ee eeee ee eeeeeeeee eeeee eeeee eeee eeeeee eeeeeeee eeee eeee eeeeeeeeeee.[‌8888‌,‌8888‌]

‌Meeeee 888‌ Meeeee-8-eeeeeeee Meeee eee eee Meeeeee Meeee[‌888‌,‌8888‌,‌8888‌]

‌Meeee 88‌ 8-Meeeeeeeeeee eeee M-Meeeeeeeeee ee Meeeeee Meeeee[‌888‌,‌888‌,‌8888‌,‌8888‌,‌8888‌,‌8888‌–‌8888‌]

Meeeeeee Meeeeeeee		Meeeeeeeee	Meeeeee	Meeee (%)	Mee
Meeeee	Meeeeeeeee Meeee
8M-eeeeee	M8M=MMMM8Me	MM		88	[‌8888‌]
8M-eeeeee	M8M=MMMM8Me	[Me(MM8)8]8MMeMe, 88% ee MeMM, ee		88	[‌888‌]
8M-eeeeee	MeMe	MeM, MMMM, ee		88	[‌8888‌]
8M-eeeeee	MMMMM8Me	MMMM, MeMe, MMM, 8°M		88	[‌8888‌]
8M-eeeeee	MeMM8(MM8)8Me	Me8MMMM8, 88% ee MMM, MM8Me8, ee		88	[‌888‌]
8,8-eeeeeeee- 8M-eeeeee	M8M=MMMM	Me8MMeMMe, eeeeeee, MeMM, 88°M		88	[‌8888‌]
8M-eeeeee	eeeeeeeeeeeee	MeMe, MMM, -88°M		888	[‌8888‌]
8M-eeeeee- 8-eeeeeeeeeeee		MeMM, M8M, ee		88	[‌8888‌]
8-eeeeee- 8M-eeeeee	eeeeeee eeeee	Me8MM8, MMMM, 88°M		88	[‌8888‌]
8M-eeeeee		8,8-eeeeeeeeeeeeee, (MMMM)8MMMM, eeeeeeeeee, 88°M		88	[‌8888‌]
8-eeeeeee- 8M-eeeeee- 8-eeeeeeeeee eeee	(MeM)8MM	MMMMM, MMM, 88°M		88	[‌8888‌]
eeeeee 8-eeeee- 8M-eeeeee-8- eeeeeeeeeee		Me8MM8, MMM, Me eeeeeeee, 88°M		88	[‌8888‌]

M-Meeeeeeeeee, eeeee ee e eeeeeeeee eeeeeeeee, eeeeee eeee eee eeeeeeeeeee ee eeeeeee ee eeeeeeeee eeeeeeee eee eee eeeeeeeeeeeee eeeeeeee eeeeeeeeee eeeeeeee eeee Meeee eeeeee eeeeee, eee eeeeeee, 8-eeeeeeeee-8M-eeeeee (‌8888‌, ‌Meeeee 888‌).[‌8888‌–‌8888‌]

‌Meeeee 888‌ Meeeeeeee ee 8-Meeeeeeee-8M-eeeeee eeee eee Meeeeeee eee Meeeee[‌8888‌–‌8888‌]

Meeeeeeeeeee Meeeeeeee

8-{[8-(Meeeeeeeeeeeee)eeeeee]eeeeee}-8M-eeeeee (‌8888‌); Meeeeee Meeeeeeee:[‌8888‌]

8M-Meeeee (‌8‌; 8.88 e, 88.8 eeee) eee eeeee ee e eeeeeee eeeeeee ee MeM (88% eeeeeeeeee ee eee; 8.88 e, 88.8 eeee) ee MMM (88 eM). Meeee M8 eeeeeeeee eee eeeeee, MMMMe (8.8 eM, 88.8 eeee) eee eeeee eeeeeeee ee 8°M. Mee eeeeeee eee eeeeeee ee eeee ee ee eee eeee, eeeee e eeeeeee 8 e, eeeeee eeee eee-eeee ee MeMMM8. Meeeeeeeee eeee Me8M eee eeeeee (MeMM8) ee eee eeeeeeee, eeee eeeeeeeeeeeee eee eeeeeeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) eeee eee eeeeeee ee ee eee; eeeee: 8.88 e (88%).

8-Meeeee-8M-eeeeee (‌8888‌); Meeeeee Meeeeeeee:[‌88‌]

Mee MMMM (888 eM) eee eeeee ee MMM (eeeeeee eeeeeee; 88.8 e, 8.8 eee) eee eee eeeeeee eee eeeeeee eee 8 eee. 8M-Meeeee (88.8 e, 8.8 eee) eee eeee eeeee eee eee eeeeeee eee eeeeeee eee 8.88 e. MeMe (88.8 e, 8.8 eee) eee eeeee eee eee eeeeeee eee eeeeee eeeeeee eee eeeeeee eee e eeeeeee 8 e eeeeee M8M (888 eM) eee eeeee. Mee eeeeeee eee eeeeeeeee eeee Me8M (8 × 888 eM) eee eeee eeeeeee eee eeeeee eeee M8M (8 × 88 eM). Mee eeeeeeee Me8M eeeeee eeee eeeee (MeMe8) eee eee eeeeeee eee eeeeee MeMe eeee eeeeeee eeeeeee eeeee eeeeeee eeeeeeee (88 Meee). Mee eeeeeee eee eeeeeeeee ee eeee eee eeeeeee; eeeee: 88.8 e (88%); ee 888–888°M/8–8 Meee; ee 88°M (MeMM).

M eeeeeee eeeeeeeee eee eeee eeeeeeee ee eeeeeeeee ee eee[‌8888‌].

8-Meeeee-8M-eeeeee (‌8888‌); Meeeeee Meeeeeeee:[‌888‌]

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

8M-Meeeee (‌8‌; 8.88 e, 88 eeee) eee eeeee ee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eeeeeeeeee Me8MM8 (8.8 e, 88 eeee), 88% ee MeMM (8 eM), eee Me8MMMM8 (8.88 e, 8.8 eeee) eee eee eeeeeee eee eeeeeee eeeee eeeeee eee ee eeeeee eeeeeeeeee ee MMM eeeeeeee. Mee eeeeeee eee eeeeeee eeee M8M, eee eee eeeeeee eeeee eee eeeeeeeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee 8-eeeeee-8M-eeeeee; eeeee: 8.88 e (88%); ee 88–88°M/8 Meee.

8-Meeee-8M-eeeeee (‌8888‌); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8M-eeeeee (‌8‌; 8.88 e, 8.88 eee) eee eeeeeeee MMM (8.88 e, 8.88 eee) eeeeeeee eeee 88-eeeee-8 (8.88 e, 8 eeee) ee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee eeeeee ee eeeeee eee 8 e eeee eeeeeeee eeeeeeee. MeM (8.8 e, 8.88 eee) eee eeeee eee eeeeeeeee eee eeeeeeeee eee 8 e. Mee eeeeeee eee eeeeeeee eeeeeee Meeeee, eee eeeeeee eee eeeeeeeeee, eee eee eeeeeee eee eeeeeeeee ee eeee 8-eeeee-8M-eeeeee; eeeee: 8.88 e (88%); ee 888–888°M/88 Meee.

References