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Please login to access the full content or check if you have access via11.15.1.2.9 Method 9: From But-2-ynedinitrile or But-2-ynediamide
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Brown, D. W.; Sainsbury, M., Science of Synthesis, (2002) 11, 542.
The addition of hydrogen bromide to but-2-ynedinitrile (177) in liquid sulfur dioxide/diethyl ether at −30 to −40°C leads to 2-bromo-3-(bromosulfanyl)butenedinitrile (178), which spontaneously cyclizes to 3,4-dibromoisothiazole-5-carbonitrile (179) in 35% yield (Scheme 58).[202,203] An identical reaction with but-2-ynediamide (180) affords 4-bromo-3-hydroxyisothiazole-5-carboxamide (181) in 44% yield.[203,204]
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References
| [202] | Meeeeeeeee, M. M.; Meeeeee-Meeeee, M. M.; Meeeeeeee, M. M., Me. Mee. Meee., (8888) 88, 888; Meee. Meeee., (8888) 88, 888888. |
| [203] | Meeeeeeeee, M. M.; Meeeeee-Meeeee, M. M.; Meeeeeeee, M. M., Me. Mee. Meee., (8888) 88, 8888; Meee. Meeee., (8888) 88, 88888. |
| [204] | Meeeeeeeee, M. M.; Meeeeee-Meeeee, M. M.; Meeeeeeee, M. M., Me. Mee. Meee., (8888) 88, 8888; Meee. Meeee., (8888) 888, 88888. |
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- 8.Meeeee-Meee, (8888) M 8e, 888.
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