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Please login to access the full content or check if you have access via10.13.1.1.1.4.1.1.5 Variation 5: From 2-(o-Amidoaryl)enol Ethers and 2-(o-Nitroaryl)enol Ethers
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Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 106.
The introduction of a 2-ethoxyalk-1-enyl substituent as in 423, in which the future α-carbon is a vinyl ether, can be achieved using Suzuki coupling (Scheme 141) of N-acetyl-o-bromoarylamines or o-iodoarylamines 421 with vinylboronate 422. Treatment of enol ether 423 with acid leads to the 1-acetyl-1H-indole 424.[363,364]
Meeeee 888 8-Meeeee-8-eeeeee-8M-eeeeee eeee e 8-Meeeee-8-(e-eeeeeeeee)eeeeee[888,888]
Meee eeeeeeee ee eeee eeeeee (e.e., eeeee eeeee eeeee, Meeeee 888), eeeeeeeee eee eeee eeeee ee eeeee eeeeeeee,[888] eeee 8-eeeee-8-eeeeeeeeeee 888, eeeee eeeeeeee 888 eeeee eeee eeeeeee ee eeeeeee 888.[888]
Meeeee 888 Meeeeee eeee 8-Meeeee-8-(e-eeeeeeeee)eeeeeee[888]
Meeeeeeeee eeee eeeeee 888 eee eeeeeeee ee eeeeeeeee eeeeeeee ee eeeeeeeeeee 888, ee eeee eeeeeeeee ee eeeeeeee ee e eeeeeeeee eeeeee eeee 8-eeee-8-eeeeeeeeeeee (888), eee eeeeee eeee eeeeee 888 (Meeeee 888).[888]
Meeeee 888 8-(8,8-Meeeeeeeeeeeee)-8M-eeeeee eeee e 8-Meeeeee-8-eeeeeeeeee eee Meeeeeeeee eeee ee Meee Meeee[888]
Me ee eeeeeeee eeeeeee, eeee eeeeeee ee e eeeeeeee eeeee 888, eeee eeeeeeee ee e eeeeeeeee(8) eeeeeeee eeeeeee, ee eeeeeeee eeeee eeeeeee(MM) eeeeeeee ee eeee 8-eeeee-8M-eeeeee (888) (Meeeee 888).[888]
Meeeee 888 8-Meeee-8M-eeeeee eeee M-Meeeee-8-[8-eeeee-8-(eeeeeeeeeeeee)eeeee]eeeeeee[888]
Me eeeeeeeeeee eeee eeeee eeeee eeeeeeeee eeeeeeee eeeeeee 888 eeeeee ee eeeeee(M)-eeeeeeeee eeeeeeee ee eee Meeeeeee eeeeeee eeee 888 eee 8-eeeee-8-eeeeeeeeeee-8-eee.[888] Meee eeeeee ee 8-eeeeee-8M-eeeeee 888 eeee eeeeeeeeeeee eeeeeeeeeeee eeee ee eeee eeeeeeeeeee ee eeeee ee Meeeee 888.
Meeeee 888 M 8-Meeeee-8M-eeeeee eeee e 8-(8-Meeeeeeee)-8-eeeeeeeeeee-8-eee[888]
Meeeeeeeeeee Meeeeeeee
8-Meeeee-8-eeeeee-8M-eeeeee (888); Meeeeee Meeeeeeee:[888]
Me e eeee ee Me(MMe8)8 (88 ee, 8.88 eeee) eee eeeeeeee MeMM (8.88 e, 8 eeee) ee MMM (8 eM) eee eeeee M-eeeeee-8-eeeeeeeeeee (888; 8.888 e, 8.8 eeee) eee 8-(8-eeeeee-8-eeeeeeeeeee)-8,8,8-eeeeeeeeeeeeeeee (888; 8.888 eM, 8.88 eeee) ee ee eee eeee eee eeeee eee eeeeeeee eee 8 e. Me eee eeeeee eeee, 8 M ee MeMM (8 eM) eee 88% M8M8 (8.8 eM) eeee eeeee eee eeee eee eeeeeee eee eeeeeeeee eeee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee). Mee eeeeeee eee eeeeee eeee eeeee, eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 8:8) eeeeee M-eeeeee-8-(8-eeeeee-8-eeeeeeeeeee)eeeeeee (888); eeeee: 8.888 e (88%); ee 88°M.
M-Meeeee-8-(8-eeeeee-8-eeeeeeeeeee)eeeeeee (888; 88 ee, 8.88 eeee) ee MMM (8 eM) eee eeeee eeee 8 M MMe (8.8 eM) eee eee eeeeeee eee eeeeeee ee ee eee 88 e. Meeeee eeeeee eeee eee eeeeeee; eeeee: 8.888 e (88%).
References
| [363] | Meeee, M.; Meeeeee, M.; Meeeee, M., Meeeeeeee, (8888), 888. |
| [364] | Meeeeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
| [365] | Meeeeeee, M.; Meeee, M.; Meeeeeee, M., Meeeeeeeeeee, (8888) 88, 888. |
| [366] | Meeeeeee, M.; Meeee, M.; Meee-eeee, M., Meee. Mee. (Meeeee), (8888), 88. |
| [367] | Meeee, M. M.; Meeeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
| [368] | Meeeeee, M. M.; Meeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [369] | Meeeeee, M. M.; Meeee, M.; Meeeee, M. M.; Meee, M.; Meeeeee, M., Mee. Meee., (8888) 8, 8888. |
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