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11.18.1.1.1.4.4 Variation 4: With Thioamides

DOI: 10.1055/sos-SD-011-01009

Ulrich, H.Science of Synthesis, (200211858.

2-Iodoaniline derivatives, such as 86, react with thiocarboxylic acid amides in the presence of palladium(0) catalysts to give 2-alkylbenzothiazoles 87 in excellent yields.[‌133‌] For example, 2-methylbenzothiazole (87, R1=X=H) is obtained in 99% yield (Scheme 34). Thiobenzoic acid amides cannot be used in this reaction, but with benzoylsulfanylcopper the cyclization is accomplished (see Section 11.18.1.1.1.4.5).

Meeeee 88 Meeeeeeeeee ee 8-Meeeeeeeeeee eeee Meeeeeeeeeeeee Meee Meeeee[‌888‌]

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8-Meeeee-8-eeeeeeeeeeeeeeeeeee (88, M8=M; M=Me):[‌888‌]

M eeeeeee ee 8-eeeeee-8-eeeeeeeeeee (88ee, 8.8eeee), eeeeeeeeeeeee (88ee, 8.8eeee), eeeeeee eeeee (8.8ee, 8.888eeee), eeee(8-eee-8,8-eeeeeeeeeeeee-8,8-eeeee)eeeeeeeeeee(8) (88.8ee, 8.88eeee), eee 8,8-eee(eeeeeeeeeeeeeeeee)eeeeeeeee ee MMM (8.8eM) eee eeeeee eeeee M8 ee 88°M eee 8e. Meeeeeeeeeeeeee eeeeeeeeee (eeeeee eee, eeeeee/MeMMe) eeee eee eeeeeee; eeeee: 888ee (88%); ee 8888°M.

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