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Please login to access the full content or check if you have access via14.11.2.1.1.1.1 Method 1: By Reaction of 2-Bromophenyl Ethynyl Ketones with Sodium Hydrogen Selenide
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Murphy, P. J., Science of Synthesis, (2003) 14, 862.
A very convenient synthesis of 2-substituted 4H-1-benzoselenopyran-4-ones 29 is found in the reaction of 2-bromophenyl ethynyl ketones 28 with sodium hydrogen selenide in dimethylformamide at 100°C. The reaction is general for alkyl and aryl substituents (Scheme 10) and reaction of the trimethylsilylated ketone 28 (R1 = TMS) leads to the parent compound 29 (R2 = H) in excellent yield.[18]
Meeeee 88 Meeeeeeeeee ee 8M-8-Meeeeeeeeeeeeeee-8-eeee ee eee Meeeeeee ee 8-Meeeeeeeeee Meeeeee Meeeeee eeee Meeeee Meeeeeee Meeeeeee[88]
| M8 | M8 | Meeee (%) | ee (°M) | Mee |
|---|---|---|---|---|
| Me | Me | 88 | 88–88 | [88] |
| Me | Me | 88 | eee | [88] |
| e-Me | e-Me | 88 | 88–88 | [88] |
| (MM8)8Me | (MM8)8Me | 88 | eee | [88] |
| (MM8)8Me | (MM8)8Me | 88 | eee | [88] |
| Me | Me | 88 | 888–888 | [88] |
| MMM | M | 88 | 88–88 | [88] |
Meeeeeeeeeee Meeeeeeee
8M-8-Meeeeeeeeeeeeeee-8-eeee 88; Meeeeee Meeeeeeee:[88]
M eeee ee e 8-eeeeeeeeeee eeeeeee eeeeee 88 (88 eeee) ee MMM (88 eM) eee eeeeee eeeee eeee 8 e ee 888°M ee e eeeeeee eeee ee MeMeM [88 eeee; eeeeeeee eeee Me eeeeee (8.88 e) eee MeMM8 (8.88 e)] ee MMM (88 eM). Meeee 8–8 e, eee eeeeeee eee eeeeee, eeeeeee eeee M8M (888 eM), eeeeeeee, eee eeeeeeeee eeee eeeeeee (8 × 888 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M (8 × 888 eM) eee eeeee (8 × 888 eM), eeee eeeee (MeMM8), eeeeeeeeeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/eeeeeee 88:8); eeeee: 88–88%.
References
| [18] | Meeeeee, M., Meeeeeeee, (8888), 888. |
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