Science of Synthesis

Williams, A. C.; Camp, N., Science of Synthesis, (2003) 14, 372.

The products, e.g. ‌72‌–‌74‌, derived from these reactions all bear a substituent at the 3-position, derived from the amine or hydrazine coupling partner. The reactions probably proceed first through formation of the 1—2 bond, cleavage of the imino functionality and closure of the 3—4 bond in an intramolecular Knoevenagel reaction. Functional groups may be introduced at the 5–8 positions by appropriate choice of 2-hydroxybenzaldehyde (‌Scheme 23‌).[‌151‌,‌169‌,‌170‌]

‌Meeeee 88‌ 8-Meeeeeeeeee 8M-8-Meeeeeeeee-8-eeee ee Meeeeeeeeeeee ee [(8-Meeeeeeeeeeeeeeeee)eeeee]eeeeeeee eee M′-(8-Meeeeeeeeeeeeeeeee)eeeeeeeeeeeeeee[‌888‌,‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeeee

8-Meeee-8-eeeeeee-8M-8-eeeeeeeeee-8-eee (‌88‌, M8 = M8 = M8 = M; M8 = MMe); Meeeeee Meeeeeeee:[‌888‌]

Meee e eeeeeee, eeeeee eeee ee eeeee eeeeeeeee eeeeeeeeeeeee (88 e, 888 eeee) ee Me8M eee eeeeeee MM8 eee eee 8 e. Meeee eeeeeee ee eee eeeeeeeeeeee MM8Me ee eeeeeeeeee eee eeeeeeee eee eeeeeee ee eeee ee ee eee eee eeeeee MM8 eeeeee eee ee eeeeeeee ee M8. M eeee ee 8-eeeeeee-8-eeeeeeeeeeeeeeeeeee (88.88 e, 888 eeee) ee Me8M (88 eM) eee eeeee eeeeeeeee, eee eeeee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeee eeeee eeeeee eee 8 e. Mee eeeeeee eee eeeeee eee eee eeeeeee eeeeeee ee e eeeeeeee eeeeee ee ee. 888 eM eee eeee eeeee ee eeeeeeeee eeeee (ee 88–88°M) eee eeeeee ee e eeeeeee eeeeeeeee. Mee eeeee eeeeeeee eeee eeeeeeee eee eee eeeeeeeeeeeeee (eeeeeeeee eeeee/Me8M 8:8) ee eeeeee eeeee [(8-eeeeeee-8-eeeeeeeeeeeeeeeeee)eeeee]eeeeeee; eeeee: 88.88 e (88%); ee 88–88°M.

Meeee [(8-eeeeeee-8-eeeeeeeeeeeeeeeeee)eeeee]eeeeeee (8.88 e, 88 eeee) eee eeeee ee e 88-eM eeeee-eeeeeeee eeeee eeeeeeeeee e eeeeeeee eeeeeee eee eeeeee eeee ee eee eeeeeeeee. Mee eeeee eee eeeeee ee ee eee eeee ee 888–888°M eeee eeeeeeee eee 8–8 e, eeee eeeeee eee MMMe8 eeeee (8 eM). Mee eeeeeeeee eeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MMMe8); eeeee: 8.888 e (88%); ee 888–888°M.

8-(Meeeeeeeeeee-8-eeeeeeeeee)-8-eeeeeee-8M-8-eeeeeeeeee-8-eee [‌88‌, M8,M8 = (MM=MM)8; M8 = MMe]; Meeeeee Meeeeeeee:[‌888‌]

8-(Meeeeeeeeeee-8-eeeeeeeeee)-M′,M′-(8-eeeeeee-8-eeeeeeeeeeeeeeeeee)eeeeeeeeeeeeee (8.88 e, 8 eeee) eee eeeeee eeee MMM (8 eM) ee 888°M eee 88 e. Mee eeeeeee eee eeee eeeeeee eeee eeeeeee eee, eee eee eeeee ee eeeeee eeeeeeee ee eeeeeeeeeeeeee (eeeeeee/eeeeeeeee eeeee 8:8) ee eeeeee eeeeee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.

References