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11.12.4.1.3 Method 3: Nucleophilic Substitution

DOI: 10.1055/sos-SD-011-00557

Boyd, G. V.Science of Synthesis, (200211467.

Oxazol-2(3H)-ones 12 are converted into 2-chlorooxazoles 341 by phosphoryl chloride,[‌220‌] and into the corresponding thiones 13 by diphosphorus pentasulfide (Scheme 149).[‌221‌]

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Mee eeeeeeee eeee ee 8-eeeeeeeeeeeeee 888 eee 888 ee eeeeeee eeeeeeee ee eeeeeeeeeeee, eeee ee eeeeeeeee eee eeeeee (Meeeee 888).[‌888‌] 8-Meeeeeeeeeeee eee eeee eeeeeeee eeeeeee eeeeeeeeeeee.[‌888‌]

Meeeee 888 Meeeeeeeeeee Meeeeeeeeeee Meeeeeee ee 8-Meeeeeeeeeeeee[‌888‌]

Mee eeeeeeeeee eeeee eeeee (eeeeeeeeeeeeeeeeeeeeeeeeee)eeeeeee (888) eeeeee eeee eeeeee-8(8M)-eeee 88 ee eeee eee eeeee eeeeee-8-eeeeeeeeeeeeee 888, eeeeeeeeeee ee eeeeeeee ee eeee eeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeee Meeeee-8-eeeeeeeeeeeeee eeee eee Meeeeeee ee Meeeee-8(8M)-eeee eeee e Meeeeeeeee Meeee[‌888‌]

8-(Meeeeeeeeeeeee)-8,8-eeeeeeeeeeeeeee (888) eeeeeeeee eeeee eeeeeeee eeee Meeeeeee eeeeeeee eeeee eeeeeeeeeeeeee eeeeeeeee ee eeeee 8-eeeee- eee 8-eeeeeeeeeeee 888 (Meeeee 888).[‌888‌]

Meeeee 888 8-Meeee- eee 8-Meeeeeeeeeee eeee 8-(Meeeeeeeeeeeee)-8,8-eeeeeeeeeeeeeee eee Meeeeeee Meeeeeee[‌888‌]

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8-Meeeee-8,8-eeeeeeeeeeeeeee (888, M8=M8=Me); Meeeeee Meeeeeeee:[‌888‌]

M eeee ee 8,8-eeeeeeeeeeeeee-8(8M)-eee (88, M8=M8=Me; 88e, 888eeee) ee MMMe8 (888eM) eee eeeeeee eeeeeeee eeee Me8M (88.8e, 888eeee) eeee eeeeeee eee eeeeeee. Mee eeeeeee eee eeeeee eeeee eeeeee eee 88e, eee eeeeee MMMe8 eee eeeeeeeee eee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeee eeeeeeeeee eeee eee. Meeeeeeeeeeeee eeee ee MeMM eee ee MeMMM8, eeeeeeee ee eeeeeeeeee eeee Me8M, eeeeeee ee eee eeeeeee eeee ee Me8MM8 eee M8M, eeeeee (Me8MM8), eeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeeeeeeee eeee eee eeeeeee; eeeee: 88.8e (88%); ee 888°M/8.88Meee; ee 88°M.

8,8-Meeeeeeeeeeeeee-8(8M)-eeeeee (88, M8=M8=Me); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8,8-eeeeeeeeeeeeee-8(8M)-eee (88, M8=M8=Me; 88.8e, 888eeee), M8M8 (88e, 888eeee), eee eeeeee (888eM) eee eeeeeeee eee 88e. Mee eeeeeeeee eeee eee eeeeeeeeeeee; eee eeeeeee eeeeeeeeeeee ee eeeeeee; eeeee: 88.8e (88%); ee 88°M.

8-Meeeeeeeeee Meeeeeee; Meeeeee Meeeeeeeee eee eee Meeeeeeee ee 8-Meeeeeeeeeeeee eeee Meeeeeeeeeee:[‌888‌]

M 8-eeeeeeeeeeeee 888 (88eeee) eee eeeee ee e eeee ee MeMMe, eeeeeeee eeee Me (8.88e, 8eeeee) eee MeMM (888eM). Mee eeee eee eeeeee eee e eeeee eeee, eeeeee, eeeeeeee eeee eeeeeeeeeeee MeMe, eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeee ee eeeeeeeeeeeeeeeee.

M eeee ee 8-eeeeee-8,8-eeeeeeeeeeeeeee (888; 8.88e, 88eeee) eee ee eeeee (88eeee) ee eeeeee eee eeeeeeee eee 8e. Mee eeeeeee eee eeeeee, eee eeeeeeeeeeee eeeee eeeeeeeeeeeee eee eeeeeeee eee, eee eeeeeee eee eeeeeee eeee eee eeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeee ee eeeeeeeeeeeeee.

Meeee Meeeee-8-eeeeeeeeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee ee eeeeee-8(8M)-eee 88 (88eeee) eee Me8M+MMMM8Me (888; 8.8e, 88eeee) eee eeeee ee eeeee eeeeeeee ee eeeeeee eeeeeee ee eeeeeee (88eM) eeee ee. 8e. Mee eeee eee eeeeeeee eee e eeeeeee 88eee, eeee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee.

8-Meeee-8,8-eeeeeeeeeeeeeee (888, M8=Me); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee eeee ee 8-(eeeeeeeeeeeeee)-8,8-eeeeeeeeeeeeeee (888; 8.8e, 8.8eeee) ee MMM (88eM) eee eeeeeee eeee e eeee ee MeMeMe (8eeee) ee Me8M; [8,8-eee(eeeeeeeeeeeeeeeee)eeeeee]eeeeeeeeeeeeee(MM) (8.888e, 8.888eeee) eee eeeee eee eee eeeeeee eee eeeeeee ee ee eee 88e eee eeee eeeeee eeee eee. ee MM8Me (88eM). Mee ee eeeee eee eeeeeeeee eeee Me8M (8×88eM), eee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Meeee eeeeeeeeeeeeee ee eee eeeeeee (eeeeee eee, eeeeeeeee eeeee/Me8M 8:8) eeee eee eeeeeee; eeeee: 8.8e (88%); ee 888888°M/8.8Meee.

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