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11.13.1.1.1.2.1 Synthesis from 2-Nitrophenols and Carbonic Acid Derivatives or Aldehydes

DOI: 10.1055/sos-SD-111-00417

Schnürch, M.; Hämmerle, J.; Stanetty, P.Science of Synthesis Knowledge Updates, (20101157.

2-Nitrophenols can be reduced to 2-aminophenols and then reacted with a C1 component and cyclized to benzoxazoles 15 in some cases in situ. One example for such an application is reduction with Raney nickel. After filtration of the catalyst, the reaction mixture is immediately reacted with cyanogen bromide (Scheme 9).[‌26‌]

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Meeeeeeeeee 8

M8 Meeee (%) ee ( °M) Mee
M 88 888 [‌88‌]
MM8Me 88 888 [‌88‌]
MM8Me 88 888 [‌88‌]

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Meeeeeeeeee 88

M8 Meeee (%) Mee
Me 88 [‌88‌]
8,8-(MeM)8M8M8 88 [‌88‌]
8-MeMM8M8 88 [‌88‌]
(MM8)8Me 88 [‌88‌]
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Meeeeeeeeeee Meeeeeeee

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Meeeee 8-Meeeeeeeeeeeeeeee-8-eeeeeeeeeee (88, M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

Meeeee 8-eeeeeee-8-eeeeeeeeeeeee (88 ee, 8.8 eeee), Me eeeee (888 ee, 8 eeee), eee MeMe8 (88 ee, 8.8 eeee) eeee eeeee ee ee eee MMM (8 eM) ee e eeeee-eeeee, M8-eeeeee eeeee-eeeeeeee eeeee. MMMMe (8.88 eM, 8 eeee) eee eeeeee eeeee eeeeeeee (MMMMMMM: ee e eeeeee eeeee, eeee eeee eeeeeeee eeeeeeeeee eeeeeeeeeeeeee eee eeeeee ee eeeeeee eee ee 8 °M). Meeee eeeeeeee eeee eeeeeee ee eeee ee ee eee 88 eee, MeMMM (88 ee, 8.8 eeee) eee eeeee, eee eeeeeeee eee eeeeeee ee eeeeeeee ee ee eee 88 e. Mee eeeeeeee eee eeee eeeeeeee eeee M8M (8 eM), eee eee eeeeeee eee eeeeeee ee eeee eee ee eeeeeeeeee 8 e. Mee eeeeeeeee eeeeeee eee eeee eeeeee eeee M8M (88 eM) eee eeeeeeeee eeee MeMMe (8 × 88 eM). Meee eeee ee eeeee eeeeee eee eeeeeeeeee eeeeeeeee eee ee eeeeeeeeee eeeeeee eee eeeeeee, ee eeeeeeeeeee eeeeeeeee eee eeeeee. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee (Me8MM8) eee eeeeeeee, eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeee eeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) eeeeeeee e eeeee eeeee; eeeee: 88 ee (88%).

References


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