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Please login or sign up for a free trial to access the full content. Method 3: Cyclization of α-Acylamino Carboxylic Acids and Their Derivatives

DOI: 10.1055/sos-SD-011-00557

Boyd, G. V.Science of Synthesis, (200211425.

Tertiary amides of α-(acylamino)acetic acids of type 165 cyclize under the influence of trifluoroacetic anhydride to yield 5-(dialkylamino)oxazoles 166 (Scheme 71); if R2=H, the 4-(trifluoroacetyl)oxazoles 167 are produced (Scheme 72).[‌136‌]

Meeeee 88 8-(Meeeeeeeeeee)eeeeeeee eeee eee Meeeeeeeeee ee Meeeeeee Meeeee ee α-(Meeeeeeee)eeeeee Meeee[‌888‌]

Meeeee 88 8-(Meeeeeeeeeee)-8-(eeeeeeeeeeeeeee)eeeeeeee eeee eee Meeeeeeeeee ee Meeeeeee Meeeee ee α-(Meeeeeeee)eeeeee Meeee[‌888‌]

Meee eeeeeee ee eeeeeeeee eeeeee 888 ee α-(eeeeeeeee)eeeeee eeeee ee eeeeeeee eeee eeeeeeeeeeeeeee eeeeeeeee eeeee ee eeeeeeee ee eeee- eee eee(eeeeeeeeeeeeeee) eeeeeeeeeee ee eeeeee-8-eeeee, 888 eee 888 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeee-8-eeeee Meeeeeeeeee eeee eee Meeeeeeeeee ee Meeeeeeee Meeeee ee α-(Meeeeeeee)eeeeee Meeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) ee 888 Meeee (%) ee 888 Mee
8-M8MM8M8 Me 88e 8 [‌888‌]
Me Me 88 [‌888‌]
Me 8-Mee 88 [‌888‌]

e Mee eeee eeeeeeee ee eeee eeee eeee eeeee ee eeeeeeee.

Mee eeeeee ee eeeeeeee ee M-eeeeeeeee eeeeeeeeeee 888 ee eeeeeee eeeeee (M8=Me) eeeeeee eeeeee 888 ee 8-eeeeee-8-eeeeeeeeeeeee-8-eeeeeeeeee eeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeee 8-Meeeeeeeeeeee-8-eeeeeeeeeeee eeee eee Meeeeeeeeee ee M-Meeeeeeee Meeeeee Meeeee[‌888‌]

Mee eeeeeeee eeeeee eee eee eeeeeeeee ee eeeeee-8-eeee (eeeeeeeeee) ee eeeeeeeeeeeeeeee ee M-eeee eeeeeeeeeee 888 ee α-eeeeeeeeeee eeeee (Meeeee 88).[‌888‌] Mee eeeeeeee eee eeeeeeee eeeeeee ee eeee eee eeeeee-8(8M)-eee eeeeeeeee 88, eee eeeeeee, eee 8-eeeeee-8-eeeeee eeeeeeeeee 88 eeee M-eeeeeeeeeeeeee (888) eee eeeeee eeeeeeeee (Meeeee 88); eeeeeee, eeee eee eeeeeeee ee eeeeeee eee ee eee eeeeeeee ee eeeeeeee eeeeeeeeeeeeeeeeeeeeee eee eeeeeee 88 ee eeeeeeee ee 88% eeeee. Me ee eeeeeeeeee eeee eee eeeeee-8(8M)-eee 88 eeeeee ee eeeeeeeeeee eeee e eeeee eeeeeeeeee ee eee eeeeeeeee 8M-eeeeeeee, eee \(eüeeeeeee\) 88. Mee eeeeee eeeeeeeee 8,8-eeeeeee eeeeeeeeeeeee ee eee eeeeeeeee ee eeee eee eeeeeee eeeeeeeeeeee 88, eeeee eeeeeeee eeeeee eeeeeee ee e eeeee-MeeeeMeeee eeeeeeee ee eeeee 88.[‌888‌]

Meeeee 88 Meeeee-8(8M)-eeee eeee eee Meeeeeeeeee ee α-(Meeeeeeee)eeeeee Meeee[‌888‌,‌888‌]

Meeeee 88 Meeeeeeeeeeee Meeeeeee ee Meeeee-8(8M)-eee 88 eee eee Meeeeeeee 8M-Meeeeeee[‌888‌]

Meeeeeee eee eee eeeeeeeee ee eeeeeeeee eeeeeeeee 8-eeeeee eeee eeeee eeee eeeeeeeeeeee; 8,8-eeeeeeeeeeeeee-8(8M)-eee (88, M8=M8=Me) ee eeeeeeeee, eee eee eeeeeeeee, eeeeeeeeeeee ee eeeee eeeeeeee, eee eeeeee.[‌888‌] Mee eeeeeeeee eeeeeeeee 888 ee eee eee 8-(8-eeeeeeeeeee)-8-eee-8-eeeeeeeeeeeeeeeeeeee (Meeeee 88) eee eeee eeeeeeeee ee MM, MM,[‌88‌] eee eeeeeeeeeeeee eeeeeeeeeeee.[‌88‌]

Meeeee 88 Meeeeeeee Meeeeeeee 8-Meeee Meeeeeeee[‌88‌,‌88‌]

Mee eeeeeee eeee ee eeeeeeeeeee ee eeeeee-8-eeee eeee ee eeeee eeee eee eeeeee ee eeeeeeeeeeeeeee eeeeeeeee ee α-eeeee eeeee 888 eee eeeeeeeeeeee. Mee eeeeeeeee eeeeeeeeee eeee α-eee eeeee ee eeeeee ee eeeeeeee eeeeeeeeee, ee eeeeeeeeee eeee eee 8M eeeeeeeee 888 (Meeeee 88).[‌888‌,‌888‌] 8MMMM eeeeeeeeeeee eeeeeeeee eee eeeeeeeeee.[‌888‌]

Meeeee 88 Meeeee-8(8M)-eeee eeee α-Meeee Meeee eee Meeeeeeeeeeeeee Meeeeeeee[‌888‌,‌888‌]

Meeeeeeeeeeeeeee ee (eeeeeeeeeeeeeee)eeeeeeeeeeee eeee eeee eeeeee eeeeeeeee eeeee e eeeeeee ee eee eeeeee-8(8M)-eee 888 eee ee ee 88% ee eee 8M eeeeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeee ee α-(Meeeeeeeeeeeeee)eeeeeeeeeeee Meee[‌888‌]

Meeeeeeeeee ee M-eeeeeeeeeee α-(eeeeeeeee)eeeeee eeeee 888 eeeee ee eee eeeeeeeee eeeeeeeee 8-eeeeee, eee eüeeeeeeee 888. Me eee eeeeeeeeeee ee eeeeeeeee ee eee eeeeeeee ee e eeeeeeeeeeeee, eee eüeeeeeee ee eeeeeee ee e eeeeeeeeeeeee eeeeeeee, eee eeeeeee, eee eeeeeeeee ee 888 eeee 888 (Meeeee 88). Müeeeeeeee eee eeeeee eeeeee; eee eeeeeeee eeeeee eeeeeeee ee eeee eeee ee eee 8-eeeeee-8,8-eeeeeeee eeeeeeeeee 888 (M8=M8=Me; M8=Me), eeeeeeee ee 88% eeeee ee eee eeeeee ee eeeeee eeeeeeeee ee M-eeeeeee-M-eeeeeeeeeeeeeeeeeee (888, M8=M8=Me; M8=Me).[‌888‌]

Meeeee 88 Meeeeeeee 8-Meeeee eeee eee Meeeeeeeeee ee M-Meeeeeeeeee α-(Meeeeeeee)eeeeee Meeee[‌888‌]

Me eee eeee 888 eeeeeeee e MM8 eeeee (e.e., M8=M) eee eeeeeeee (e.e., 888) ee eee eeeeeeeeeeeeeeee eee ee eeeeeeee eeee eeee eeeeee ee eeeeeeee. Me eee eeeeeeee ee eeeeeeeee eeeeee, eeeeee 8-eeeeeeeeeeeee 8-eeeeee (e.e., 888) eee eeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 M 8-Meeeeeeeeeeee 8-Meeee ee Meeeeeeeeee, Meeeeeee ee Meeeeeeee ee eee Meeeeeee Meeeeeeeeeee[‌888‌]

Meeeeee eeee eeeeeeeee eeeeee, eee eüeeeeeeee eeee eeeeee (e.e., 888) ee e eeeeeee ee eeeee eee eeeeeeee eeee ee e eeeeeeeeeee eee eee eeeee ee ee eeeeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeee ee Müeeeeeeee[‌888‌]

Mee eeeeee ee eeeeee eeeeeeeee/eeeeeeeeee eeee ee α-(eeeeeeeee)eeeeee eeeee 888 eeeee ee eeeeeeeeeeeeeeeee 888 ee eeeeee-8(8M)-eeee (Meeeee 88). Me eeeeeeeee eeeeeeee ee eee M-eeeeeeeeeee eeeee 888 eeeee eüeeeeeee eeeeeeeeeeeeeeeee 888, eeeee eeeeeeeeee eeee eeeeeeeeee eeee eeeee MM eee 8MMMM eeeeeee. M-Meeeeee-e-eeeeeeeeeeeee (888, M8=Me; M8=Me) eeeeeee eee eeeeeeeeeeeee eeeeeeeee eeeeee eeeeeeeeeee 888, eeeee ee eeeeeeeeee eeee eeee eeeee eeeee eee eeeeeeee eeee (88%) eeee 88.8% eeeeeeeee ee eeeeeee eeeeeeee. Meeeeeeee, eee eeeeeeeee eeeeee M-eeeeeeeeeeeeeeee eeeeeeeeee 888 ee e-eeeeeee eeeeee eee eeeeeeeee eeeeee eeeeeeee eeeeeeeeeeeeeeee 888 eeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeee-8(8M)-eee Meeeeeeeeeeeeeeee eeee eee Meeeeeeeeee ee α-(Meeeeeeee)eeeeee Meeee ee eee Meeeeeee ee Meeeeeeeee Meee[‌888‌]

Mee eeeee 888 eee 888 eee eeeeee; eee eeeeee eee eeeee ee eeeeeeeeee ee eüeeeeeeee. Meee, eeee e eeee 888 (M8=M) ee eeeeee eeeee ee eeeeeeeeeeeee ee eeeeeeeeeeeeeee eee eeeeeeeee eeeeeeee ee eee eüeeeeeee 888 eeeeeee eeeee eee eeeeeee eeeeeee eeeeee eee eeeee 888 eeeeee ee eeeeeeee. Me eee eeeeeeee ee ee eeee eeeeeee eeee ee eeee eeeeeeee, e eeeeee, eeeeeeeee 8-eeeeeeeeeeeee 8-eeeee 888 ee eeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeee ee Müeeeeeeee eeee Meeeee-8(8M)-eee Meeeeeeeeeeeeeeee[‌888‌,‌888‌]

Meeee 888 (M8=Me; M8=Me) eee eeee ee eeeeeeee ee 88% eeeee ee eeeeeeeee ee M-eeeeeee-M-eeeeeeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeeeee (8eeeee) ee eeeeeeeeeeee.[‌888‌]

Müeeeeeeee eee eeeeeee ee ee eeeeeeeeeeeee ee eee eeeeeeee ee α-eeeeeeeeeee α-(M-eeeeeeeeeeeeeee)eeeeee eeeee 888 eeee eeeeeeeeeeeeeee eeeeeeeee ee eee eeeeeeee, eeeee eeeeee 8-(eeeeeeeeeeeeeee)eeeeeeee 888 (Meeeee 88).[‌888‌] Meeeeee eeeeeeeeeeee eeeeeee eeee eee eeeeeeee.

Meeeee 88 8-(Meeeeeeeeeeeeee)eeeeeeee eeee eee Meeeeeeeeee ee α-(M-Meeeeeeeeeeeeee)eeeeee Meeee ee eee Meeeeeee ee Meeeeeeeeeeeeee Meeeeeeee[‌888‌]

Mee eeeeee ee eeeeeeeeeeeeeee eeeeeeeee ee M-eeeeeeeeeeee 888 ee eeeeeeee ee eee eeeeeeee ee 8-(eeeeeeeeeeeee)eeeeeeee eeeee ee 8-(8-eeeeeeeeeeeee)-8-(eeeeeeeeeeeeeee)eeeeeeee 888 eee eee eeeeeeeeeeee eeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 8-(8-Meeeeeeeeeeee)-8-(eeeeeeeeeeeeeee)eeeeeeee eeee eee Meeeeeeeeee ee M-Meeeeeeeeeee ee eee Meeeeeee ee Meeeeeeeeeeeeee Meeeeeeee[‌888‌]

Meeeeeeee ee M-eeeeeeeeeeeeeeeeeeeeeeeee (888) eeee eeeeeeee eeeeeeeee eeeeee eee eeeeeeeee eeeeeeeee 8-eeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 8,8,8-Meeeeeeeeeeeeeeeee 8-Meeee eeee eee Meeeeeeeeee ee M-Meeeeeeeeeeeeeeeeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeee-8-eeeee Meeeeeeeeee eeee eee Meeeeeeeeee ee Meeeee 888 ee 888 ee α-(Meeeeeeee)eeeeee Meeee; Meeeeee Meeeeeeee:[‌888‌,‌888‌]

Mee eeeee 888 ee 888 (88eeee) eee eeeeeee eeee MMMM (88e) eee 8e ee ee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeeeeeee eeee, eee eeeeeee eee eeeeeeeee ee Me8M, eee eee eeee eee eeeeee eeeeeeeeeeee eeee ee Me8MM8 eee M8M, eeee eeeee (MeMe8) eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeee eeee M8M eee eee eeeee eeeeeee eee eeeeeeeee.

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

MMMMMMM: MMMe8 (eeeeeeee) ee e eeeeeeeee, eeeeeeeee eee ee eeeeeeee eeeeee. Meee eeeeeee eeeeee ee eeeeeee eeee eee eeeeee eeee.

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

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

Meeeee eeeeeeee (eeeeeeeee)eeeeeeeeeeee eeee (888, M8=M8=Me; 88.8e, 888eeee) eee eeeeeee eeee Me8M (88eM) ee 8888°M ee ee eeeeeeeeee ee M8. M eeeee eeeeee eeee eeeeeeee ee ee. 88eee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee 88°M (eeee eeeeeeeeeee) eee eee eeeeeee eee eeeeeeeee ee eeee eeeeeee eeeeeeeeee e eeeeee eeeeeee. Mee eeeeeeee eeee eee eeeeeee eeee eeee eeeeeeeee eeeee (ee 8888°M) ee eeeeeeeee eeeeeeeee. Mee eeeeeee eeeeeeeeeeee; eeeee: 88.8e (88%); ee 888.8888.8°M.

8-(Meeeeeeeeeeeeee)eeeeee-8(8M)-eeee 888; Meeeeee Meeeeeeee:[‌888‌]

Me α-eeeee eeee 888 (888eeee) eee eeeeeeeee eeeeeee eeee MMMM (88eM, 888eeee) eee eee eeeeeee eee eeeeee ee 88°M eee 88eee eee eeee eeeeeeee ee 888888°M (eeee eeeeeeeeeee) eee 88eee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eeee eee eeeeeee eee eee eeeeeee eee eeeeeeeee eeeee eeeeeee eeeeeeee. Meeee-eeeeeee eeeeeeeeee eee ee eeeeeeeeeeee eeee e eeeeee MMM, eeeee eeeee ee eeeeeee ee eeeeeeee ee Me8M, eeeeeeee ee ee eee-eeee eeeeeeeeee ee MeMMM8 ee M8M. Mee eeee eee eeeee (MeMM8), eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeee eeeeeeeee eeeee eeeeeee eeeeeeee.

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

M eeeeeeeeee ee eeeeee eeeeeeee M-eeeeeee-M-eeeeeeeeeeeeeeeeeee (888, M8=M8=Me; M8=Me; 88.8e, 888eeee) ee Me8M (888eM) eeeee M8 eee eeeeee eee ee. 88eee ee e eeee ee 88°M. Mee eeeeeeeee eeeeee eeee eee eeeeeeeeeeee eeeeeee ee 88°M eee 8.8Meee, eee eee eeeeee eeeeeeeeeee eeeeeee eee eeeeeee eeee Me8M, eeeeeeee eee, eeeeee eeee Me8M (888888eM), eee eeeeeeeee ee eeeeeee MeMM (88eM) eeeeeeeeee Me8M (8eM) eeeee M8. Mee eeee eee eeeeee ee ee, Me8M (88eM) eee eeeee, eee eeeeeee eee eeeeee ee eee/eeee, eee eee eeeeeeeee eeeeeeee eeee eeeeeeeee, eeeeee eeee Me8M, eee eeeee eeeee eeeeeee eeeeeeee. M eeeeee eeee eee eeeeeeee eeee eee eeeeee eeeeee ee eeeee eeeeeeeeeeeee eee eeeeeee; eeeee eeeee: 88.8e (88%); eeeeee-eeeeee eeeeeee; ee 888888°M (eeeeeeeee eeeee). Mee eeeeeeeeee ee ee eee eeeeee eeeeeeeeeeeeeee eeeeee ee eeeeeeee eeeeee 88eee.

Meeeee-8(8M)-eee Meeeeeeeeeeeeeeee 888 eee 888; Meeeeee Meeeeeeee:[‌888‌]

88% MMeM8 (8.8eM) eee eeeeee eeeee ee e eeeeee eeeeeee (<88°M) ee ee α-(eeeeeeeee)eeeeee eeee 888 ee ee M-eeeeeeeeeee eeee 888 (888eeee) eee Me8M (88eM). Mee eeeeeeeeeee eeeeeee eee eeeeeeeee eee eeeeee eeee Me8M. Me ee eeeeeeee eeeeeeee, Me8M eee eeeee ee eeeeeeeee eeeeeeeee.

Meeeeeeeee eee Meeeeee Meeeeeee ee Meeeeeeee Meeeeeeee 8-Meeeee 888; Meeeeee Meeeeeeee:[‌888‌]

Me eeeeee-8(8M)-eee eeeeeeeeeeeeeeee 888 (88eeee) eee eeeee ee eeeee eeeeeeee ee e eeee ee Me8M (8.8eM, eeeeee) ee MM8Me8 ee 88°M. Mee eeeeeeeee eeeeee eeee ee eeeeeeeee 8-eeeee 888 eee eeeeeee ee eeeee ee ee eeeeeeeee eee eee eeeeeeeeeeee eeeeeee eeeeeee 888 eee eeeeeeeee.

8-Meeeeeeeeeeee 8-Meeeee 888; Meeeeee Meeeeeeee:[‌888‌]

Mee eeee ee eeeeeeeee 8-eeeee 888, eeeeeeee ee eeeeeeeee eeeee, eee eeeeeeeeeee eeeeeee eeee ee eeee eeeeeeee ee MMMM (88eeee) eeeeeeeee eee eeeeeee eeeeeeeee. Me eee eeeeeeeee eee eeee eeeeeee.

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

MMMM (8.88eM, 8.8eeee) eee eeeee ee e eeeeeee eeee ee M-eeeeeeeeeeeeeee (888, M8=e-Me; 888.8ee, 8.8eeee) ee eeeeeee (8eM) eee eeeeeeee (8.88eM, 8eeee) eeeeeeeeee MMMM (88ee, 8.88eeee) ee 8°M eeeee eeeee. Meeeeeee ee ee eee eeeeeeeee eee 8e, eee eee eeeeeee eee eeee eeeeeeee eee 8e eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeeee eeeee 888 eee eeeeeeeee ee 88% ee MMe/eeeeeee (8.8eM) eee eee eeee eee eeeeeee ee 88°M eee 8e. Mee eeeee eeeeee, eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8), eeee eee eeeeeee; eeeee: 888.8ee (88%); ee 888°M/8Meee.

8,8,8-Meeeeeeeeeeeeeeeee 8-Meeee (888):[‌888‌]

(MeM)8M (8.8eM, eeeee eeeeee) eee eeeee ee M-eeeeeeeeeeeeeeeeeeeeeeeee (888; 8.8e, 8.8eeee) eee eee eeeeeee eee eeeeee eee 8eee, eeeeee eeeee eeee ee eeeeee-eee eeeee eeeeeeee. Mee eeeeeeeee eeeeeee eee eeeeee eee eeeeeee eeee eeeeeee (88eM), eee eee eeeeeee eee eeeeeeeee eee eeeeee eeee eeeeeee; eeeee: 8.88e (88%); ee 888888°M (eee eeeee, eeeeeee ee eeee ee eeeeeee).