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Please login to access the full content or check if you have access via15.5.1.1.1.5.2.1.1 Variation 1: From N-Acyl-2-aryl-2-hydroxyethylamines: Pictet–Gams Modification of the Bischler–Napieralski Synthesis
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Álvarez, M.; Joule, J. A., Science of Synthesis, (2005) 15, 720.
The modification introduced by Pictet and Gams[193,194] allows the direct synthesis of an aromatic isoquinoline 212, although the starting materials 210 are not quite as straightforwardly available. The presence of a hydroxy (or methoxy) group at the future isoquinoline C4 means that following ring closure, a simple dehydration (or loss of methanol) from 211 gives the aromatic molecule 212 (Scheme 97).
Meeeee 88 Meeeeeee Meeeeeee ee eee Meeeee–Meee Meeeeeeeeeee ee eee Meeeeeee–Meeeeeeeeee Meeeeeeee Me Meee Meeeeeeeeeeee[888,888,888]
Me eeee eeeee, eee eeee-eeeeee eeeeeee eeee eee eeee eeeeeeee eeeeeeeeee, eee e eeeeeeee eeeeeeeee eeee eeee ee eeeeeeee, eee eeeeeee, ee Meeeee 88 eeeeeeee ee 888 eee 888 eee eeeeeeee eeee eee eeee eeeeeee.[888]
Meeeee 88 Meeeee–Meee Meeeeeeee Meeeeee e Meeeeeee Meee eee Meeeeeeeeeeee[888]
M eeeeeeeee eeeeeee eeee eeee eeeeee ee eee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeeee ee eeee eeeeeeeeeeeee, eeeeee eeee eee eeeeeeeeeeee. Meee eeeeeeeeeee eeeeeee eee eeee eeeee eee eeeeeeee eeeeeeeee ee eeeeeee ee eeeeeeeeeee eeeeeeee; eee eeeeeee, eee eeeeeeeeee eeeeeeeee eeeeeeeeeee ee 888 (M8 = Me, Me) eeeee eee eeeeeeeeeeeee 888 ee eee eeeeeeee, eee eeeeeeeeeee ee 888 (M8 = Me, Me) eeeee eee eeeeeeeeeeeee 888 (Meeeee 88). M eeeeeeee eeeee eee eee eeeeeeeee ee 888 ee eeeee.[888]
Meeeee 88 Meeeeeeee ee Meeeeee ee eee Meeeee–Meee Meeeeeeee[888]
Meeeeeeeeeee Meeeeeeeee
8,8-Meeeeeeee-8,8-eeeeeeeeeeeeeeeeeeee [888, M8 = 8,8-(MMe)8; M8 = M8 = Me]; Meeeeee Meeeeeeee:[888]
M-(8-eeeeeeeeeee)eeeeeeeee 888 [M8 = 8,8-(MMe)8; M8 = M8 = Me; 8.8 e, 88 eeee] eee MMMe8 (8 eM, 88 eeee) eeee eeeeeeee ee MMMe8 (88 eM) eee 8 e, eeee eeeeee eeee eee M8M eee eee eeeeeee eeee eeeeeeee eeee 88% ee MeMM. Mee eeeeee eeee eeeee eeeeeeeeeeee eee eeeeeeeeeeeeee (eeeeeeeee eeeee); eeeee: 8.88 e (88%); ee 888.8°M.
8-Meeeee-8-eeeeeeeeeeeeeeeeee (888, M8 = Me); Meeeeee Meeeeeeee:[888]
M-(8-eeeeeee-8-eeeeee-8-eeeeeeeeeee)eeeeeeeee (888, M8 = Me; 8 e, 8 eeee), M8M8 (8 e, 88 eeee), eee MMMe8 (88 e, 88 eeee) eeee eeeeeeee ee eee eeeeee (88 eM) eee 8 e. Mee eeeeee eeeeeee eee eeeeee eeee eee eee eeeeee eeee eeeeeee (MMMMMMM: eeeeeeeeee) eee eeee eeee eeeeeeee eeee 88% ee MeMM eee eeeeeeeee eeee eeeeeee. Mee eeeeeee eee eeeee eee eeeeeeeeee eee eee eeeeeeeeeeee eeeeeeeee eeee eee eeeeeeeeeeeee eeee eeee MMe(e), eee eeee eeeee eeeeeeee ee eeeeeeeeeeeeeeeee (eMeMM/eeeeeeeee eeeee); eeeee: 88%; ee 888°M (eee).
References
| [177] | Meeeee, M. M.; Meeeeeeeeeee, M. M., Mee. Meeee. (M. M.), (8888) 8, 88. |
| [193] | Meeeee, M.; Meee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
| [194] | Meeeee, M.; Meee, M., Mee. Meeee. Meee. Mee., (8888) 88, 8888. |
| [195] | Meeeee, M. M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [196] | Meeee, M. M.; Meeeeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 888. |
| [197] | Mee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [198] | Meeeeeeeee, M.; Meeeee, M. M.; Meeee, M. M.; Meeeee-Meeeeee, M., Meeeeeeeeee Meee., (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 8e, 888.
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