Science of Synthesis

Ambhaikar, N. B., Science of Synthesis Knowledge Updates, (2020) 2, 194.

Unsymmetrically substituted phenazines are generally challenging synthetic targets. However, they are often accessible from the corresponding unsymmetrical halophenazines.[‌16‌,‌17‌] Chlorophenazines are a useful class of compounds that provide an entry to several functionalized phenazine derivatives through nucleophilic substitution and other related reactions.[‌18‌–‌24‌] An interesting and efficient method for the synthesis of 1-chlorophenazines is based on the use of 3,6,6-trichloro-2-hydroxycyclohex-2-en-1-one (‌1‌), which is the synthetic equivalent of 3-chlorocyclohexa-3,5-diene-1,2-dione (‌2‌; ‌Scheme 3‌).[‌25‌]

‌Meeeee 8‌ 8,8,8-Meeeeeeee-8-eeeeeeeeeeeeeee-8-ee-8-eee ee e Meeeeeeee Meeeeeeeee ee 8-Meeeeeeeeeeeeee-8,8-eeeee-8,8-eeeee[‌88‌]

Meeeeeeeeeeeeee eeeeeeeee ee 8,8,8,8-eeeeeeeeeeeeeeeeeeeeee-8,8-eeeee (‌8‌) eeeee e eeeeeeee eeeeeeee eeeeeeeee ee e eeeeee eeeeee eeeeee 8,8,8-eeeeeeeee-8-eeeeeeeeeeeeeee-8-ee-8-eee (‌8‌) ee e eeeeee eeeeeee eeeeee eeeeeeeeeeeeee. Meee eeeeeee ee eeeeeeeee ee e eeeeeeeeee eeeeeeeeeeee eeeeeeee eeee eeeeeee-8,8-eeeeeeee (8,8-eeeeeeeeeeeeeeeee) ‌8‌ ee eeee 8,8,8-eeeeeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeee eeeeeeeeeee ‌8‌, eeeee eee eeeeeee eeeeeee eeee 8,8-eeeeeeee ee eee eeee ee eeeee 8-eeeeeeeeeeeeeeee ‌8‌ (‌Meeeee 8‌).

‌Meeeee 8‌ Meeeeeeee ee 8-Meeeeeeeeeeeeee Meeeeeeeeee[‌88‌]

‌Meeeeeeeeee 8‌

Mee eeeeeeeeeeeeeeeeeeeeeeeeeee eeeeeeee eeeeeeee ‌8‌ ee eeeeeeeeee eeeeeeeeeee eee eeeeeee eeeeeeeee; ee eee ee eeeeeeee eeeeeeee ee eeeeeeeeeeee ee eeeeeeeeeeee eeeeeeeee eeeee-eeeeeeeeeee-8,8-eeee.[‌88‌] Mee eeeeeeeeeeee eeeee eeee eeee eee ee eeeeeee ee eeeeee ee eeeeeeeeeeeeee eeeeee eeeee, eeeee ee eeeeee ee e eeeeeeeee, ee eeeee eee eeeeeeee ee eeeeeeeeee, eeeeeeeeee eee eeeeeeeee eeeeeeeee ‌8‌ ee eeee eeeeee. Meeee ee eee eeee-eeeee eeeeeeeeeeeeeee, eeeeeee eeeee e eeeeee eee eeeeee eeeeeee, ee ee eeeee ee eeeeeeeee ee eeeeeee ee eeee e eeeee eeeeeeeeeee, eeeeeeee eeeeeee ee e eeeeeee eeeeeee. Meeeeee, eeeeeeeee ee eee eeeeeeeee eeeeeeeeeeeee ‌8‌ eeee 8,8-eeeeeeee eeeeee eeeee eeeeeeeeeeeee, eeeeeeee eee eeeeeee 8-eeeeeeeeeeeeeeee ‌8‌ ee eeee eeeeee.

Meeeeeeeeeee Meeeeeeee

8,8,8-Meeeeeeee-8-eeeeeeeeeeeeeee-8-ee-8-eee (‌8‌):[‌88‌]

Mee eeeeeeeee eeeeeeeeeeee ee 8,8,8,8-eeeeeeeeeeeeeeeeeeeeee-8,8-eeeee (‌8‌) eee eeeeeee eee eeeee e eeeeeeee eeeeeeee eeeeeeeee ee e eeeeeeeeee eeeeeeeeeee eeee eeee eee eeeeeeeeeeee eeeeeeeee ee e eeeeeeee eeeee eeee (eeeeee) eeeeeeeee. M eeeeeee eeee (eeeeeeee 8 ee; Meeeee-eeeeeeeee eeeeeeee ee eee eeee ee eee eeee) eee eeee ee eee eeeeeee eee e eeeeeeee eeeee eee eeee ee eee eeeee. Mee eeeeeee eeeeeeeee eee 888 eM ee eee eeeeeeeee, eee 88 eM ee eee eee. Mee eeee eeeeeee eeeeeeee eeeee 8 M. Mee eeeeeeeee eee eeeeeeeeeeee eeeeeee. Mee eeeeeeeeeee eee eeee ee eeeeeeeeeeeee 88 °M ee eeeeeeee eeeeeee. Mee eeeeeeeee eee eeeeeeeee ee e eeeeeee ee MeMM (88 eM)/MeMM (88 eM)/MeMeM8 (8 e); 88 eM eee 88 eM ee eeee eeeeeee eeee eeeeee ee eee eeeeeeee eee eee eeeeee eeeeeeeeeeee, eeeeeeeeeeee. MeMMe (8.8 e) eee eeeeee ee eee eeeee eeeeeeeeeee. M eeee ee 8,8,8,8-eeeeeeeeeeeeeeeeeeeeee-8,8-eeeee (‌8‌; 8 eeee) eee eeeeeeeeeeee eeeee e eeeeeeee eeeeeeeee ee 88.88 M eeeeee MMM. Mee eeeeeeeeeee eeeeeeeeeee eee 8 M/eee. Mee eeeeeee eee eeeeeeee ee eeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee. M8M (888 eM) eee eeeee ee eee eeeeeee eee eee eeeeeee eee eeeeeeeee eeee MMMe8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeee M8M, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeeeeeee (eeeeeeeee eeeee) ee eeee eee eeeeeee ee eeeee eeeeeee; eeeee: 88%.

8,8,8-Meeeeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeeee ‌8‌; Meeeeee Meeeeeeee:[‌88‌]

M eeee ee 8,8,8-eeeeeeeee-8-eeeeeeeeeeeeeee-8-ee-8-eee (‌8‌; 8.88 eeee) eee e eeeeeee-8,8-eeeeeee ‌8‌ (8.88 eeee) ee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee eeeeee ee eeeeee eeee e Meee–Meeee eeee eee 88 e. Mee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeee eeee Me8M (88 eM). M eeeee eeeeee ee e eeeee eeeee eeeeeeeee ee eeeeeeeeee eee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeeeeeeeeee eee eee eeeeeee eee eeeeeeee eeeeee ee eeeeeeeeeeeeeee eeee ee eeeeeeeeeee eeeeeee ee ee eeeeee eeeeeeeeeeeeee ee eeee eee eeeeee eeee eeeeeee.

8-Meeeeeeeeeeeeeee ‌8‌; Meeeeee Meeeeeeee:[‌88‌]

M eeee ee e 8,8,8-eeeeeeeee-8,8,8,8-eeeeeeeeeeeeeeeeeee ‌8‌ (8.8 eeee) ee MMM (88 eM) eee 8,8-eeeeeeee (8 eM) eee eeeeee ee eeeeee eee 8 e, eeee eeeeee, eee eeeeee eeee eeee eeeee (888 eM). Mee eeeee eeeeeeee eeee eeeeeeeee ee eeeeeeeeee, eeeeee eeee eeee M8M, eeeee, eee eeeeeeeeeeee eeee ee eeeeeeeeeee eeeeeee.

References