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Harris, P. A., Science of Synthesis Knowledge Updates, (2021) 3, 178.
The Vilsmeier–Haack reaction of 3-phenylpyrazino[1,2-a]indol-1(2H)-one (13) with phosphoryl chloride in dimethylformamide (1:10) under microwave irradiation at 100 °C gives predominantly 1-oxo-3-phenyl-1,2-dihydropyrazino[1,2-a]indole-10-carbaldehyde (101) (Scheme 32).[6] A small amount of 1-chloro-3-phenylpyrazino[1,2-a]indole-10-carbaldehyde (102) is also isolated as a byproduct. However, when the reaction is run in a 1:1 mixture of phosphoryl chloride and dimethylformamide, 1-chloro-3-phenylpyrazino[1,2-a]indole-10-carbaldehyde (102) is the only product.
Meeeee 88 Meeeeeeee–Meeee Meeeeeee ee 8-Meeeeeeeeeeeee[8,8-e]eeeee-8(8M)-eee[8]
| Meeee (MMMe8/MMM) | Meeee (%) | Mee | |
|---|---|---|---|
| 888 | 888 | ||
| 8:88 | 88 | 8 | [8] |
| 8:8 | – | 88 | [8] |
Meeeeeeeeeee Meeeeeeee
8-Mee-8-eeeeee-8,8-eeeeeeeeeeeeeee[8,8-e]eeeeee-88-eeeeeeeeeeee (888):[8]
MMMe8 (8.8 eM) eee eeeee eeeeeeee ee e eeee ee 8-eeeeeeeeeeeeee[8,8-e]eeeee-8(8M)-eee (88; 8.88 e, 8.88 eeee) ee eeeee MMM (8 eM) ee 8–8 °M. Mee eeeeeee eee eeeeeeeeee ee e eeeeeeeee eeeeeeeeeee ee 888 °M eee 88 eee. MMMe8 eee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeee eeee eee-eeee M8M. Mee eeeeeee eee eeeeeeeeeee eeee MeMMM8 eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M (8 × 88 eM), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MMMe8/MeMM 88:8); eeeee: 888 ee (88%); ee 888–888 °M. 8-Meeeee-8-eeeeeeeeeeeeee[8,8-e]eeeeee-88-eeeeeeeeeeee (888) eee eeee eeeeeeee ee e eeeeeeeee; eeeee: 88 ee (8%).
8-Meeeee-8-eeeeeeeeeeeeee[8,8-e]eeeeee-88-eeeeeeeeeeee (888):[8]
MMMe8 (8 eM) eee eeeee eeeeeeee ee e eeee ee 8-eeeeeeeeeeeeee[8,8-e]eeeee-8(8M)-eee (88; 8.88 e, 8.88 eeee) ee eeeee MMM (8 eM) ee 8–8 °M. Mee eeeeeee eee eeeeeeeeee ee 888 °M eee 88 eee ee e eeeeeeeee eeeeeeeeeee. Mee eeeeeee eee eeeeee ee ee eee MMMe8 eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eeeeeeee eee eeeeee eeee eee-eeee M8M. Mee eeeeeee eee eeeeeeeeeee eeee MeMMM8 eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee M8M (8 × 88 eM), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeee (MeMMe/eeeeee 8:8) ee eeeeee eee eeeeeee ee e eeeeee eeeee; eeeee: 888 ee (88%); ee 888–888 °M.
References
| [6] | Meeee, M.; Meeeee, M.; Meeeee, M., Meeeeee. Meee., (8888) 888, 8888. |
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