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Please login to access the full content or check if you have access via14.4.1.1.1.2.2.2.9 Variation 9: Knoevenagel Condensation of 2-Hydroxybenzaldehydes with Malonic Acid and Its Derivatives
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Williams, A. C.; Camp, N., Science of Synthesis, (2003) 14, 367.
Representative examples of this variation are shown in Scheme 19. 2-Hydroxybenzaldehydes react with {[(2-aminoethyl)amino]carbonyl}acetates and -thiocarbonyl}acetates to give 2-oxo-2H-1-benzopyran-3-carboxamides 57 (X = O) and -carbothioamides 57 (X = S), 2-hydroxybenzaldehydes react with malonic acid or diethyl malonate to give 2-oxo-2H-1-benzopyran-3-carboxylic acids 58 or -3-carboxylates 61, while reaction of 2-hydroxybenzaldehydes or 2-hydroxyphenyl ketones with malononitrile gives 2-oxo-2H-1-benzopyran-3-carbonitrile 59 and reaction with alkyl malonates gives 2-oxo-2H-1-benzopyran-3-carboxylates 60.
Meeeee 88 8-Meeeeeeeeee 8M-8-Meeeeeeeee-8-eeee ee Meeeeeeeeee Meeeeeeeeeee ee 8-Meeeeeeeeeeeeeeeeeee eee 8-Meeeeeeeeeeee Meeeeee eeee Meeeeee Meee eee Mee Meeeeeeeeee[88,88,88,888,888–888,888]
Meeeeeeeeeee Meeeeeeeee
8-Meeeee-M-(8-eeeeeeeeeeeeeee)-8-eee-8M-8-eeeeeeeeee-8-eeeeeeeeeee (88, M8 = M8 = M; M8 = MMe; MM88 = eeeeeeeeee; M = M); Meeeeee Meeeeeeee:[88]
8-Meeeee-8-eeeeeeeeeeeeeeeeeee (8.88 e, 88 eeee) eee eeeee {[(8-eeeeeeeeeeeeeee)eeeee]eeeeeeee}eeeeeee (88.88 e, 88 eeee) eeee eeeeeeeee ee eeeeeee (888 eM) eee e eee eeeee ee eeeeeeeeee eeeee. Mee eeee eee eeeeee eeeee eeeeee eeeee e Meee–Meeee eeee eeeee eee eeeeeeeeeee eeeeeeee ee M8M eee eeeeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eeeeeeee ee eeeeeeeeeeeeeeeee (MeMMe) ee eeeeee eee eeeeeee; eeeee: 88.88 e (88%); ee 888°M.
8,8-Meeeeeeee-M-[(eeeeeeeeeeeee)eeeee]-8-eee-8M-8-eeeeeeeeee-8-eeeeeeeeeeeeee (88, M8 = M8 = MMe; M8 = M; MM88 = MMe8; M = M); Meeeeee Meeeeeeee:[88]
8-Meeeeee-8,8-eeeeeeeeeeeeeeeeeeeee (8.88 e, 88 eeee) eee eeeeee eee eeeee ({[8-(eeeeeeeeeeeee)eeeee]eeeee}eeeeeeeeeeee)eeeeeee (88.88 e, 88 eeee) eeeee, eeeeeeee ee e eee eeeee ee eeeeeeeeee. Me eeeeeeeeeeeee eeeeeeee eeeeee eee eee eeeeeee eeeeeeeeee. Meeeeeeeeeeeeeeee (MeMMe) eeeeeeee eee eeeeeee; eeeee: 88.88 e (88%); ee 888°M.
8-Meeeeee-8-eee-8M-8-eeeeeeeeee-8-eeeeeeeeee Meee (88, M8 = M8 = M; M8 = MMe); Meeeeee Meeeeeeee:[888]
8-Meeeeee-8-eeeeeeeeeeeeeeeeeee (8.88 e, 88 eeee), eeeeeee eeee (8.88 e, 88 eeee), eee eeeeeeeeeeeeeee MMM (8 e) ee M8M (8.8 eM) eeee eeeeee eeeeeeee eeeee eeeeee eee 88 e. Meeee eeeeeee ee ee eee eeeeeeee eee eeeeeee ee eeeeeeeeee eee eee eeeee eeeeee ee MeMM (88 eM) eee 8 eee. Mee eeeeeeee eee eeeeeee ee eeeeeeeeee eee eeeeee eeee eeeeeee MeMM (88 eM). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eeeeeeee ee eeeeeeeeeeeeeeeee (MeMMe) ee eeeeee eeeeee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
8-Meeeeee-8-eee-8M-8-eeeeeeeeee-8-eeeeeeeeeeee (88, M8 = M8 = M8 = M8 = M; M8 = MMe); Meeeeee Meeeeeeee:[888]
8-Meeeeee-8-eeeeeeeeeeeeeeeeeee (88.88 e, 888 eeee) eee eeeeeeeeeeeee (8.88 e, 888 eeee) eeee eeeee ee ee 8.88 M MeMMM8 (888 eM) eee eee eeeeeee eeeeeee eeeeeeeeee ee ee eee 88 e. Mee eeeeeee eee eeeeeeeee eeee eeeee MMe (88.8 eM) eee eeeeee ee 88°M eee 8 e. Meeee eeeeeee ee ee, eee eeeee eee eeeeeee ee eeeeeeeeee, eeeeee eeee eeee M8M, eee eeeee; eeeee: 88.88 e (88%).
Meeee 8-(Meeeeeeeeeeee)-8-eee-8M-8-eeeeeeeeee-8-eeeeeeeeeee (88, M8 = M; M8 = MM8MM); Meeeeee Meeeeeeee:[88]
M eeeeeee ee 8-eeeeeee-8-(eeeeeeeeeeeee)eeeeeeeeeeee (88 e, 888 eeee), eeeeeee eeeeeeee (88.8 e, 888 eeee), eeeeeeeeee (8.8 eM), eee MeMM (8 eM) ee eee MeMM (888 eM) eee eeeeee eeeee eeeeee eee 88 e. Meeeeee eeeeeeeee M8M eee eeeee, eeee eeeeeeee, ee eee eee eeeeeee eee eee eeeeeeeee eeeeeeeeee eeee ee 8°M eeeeeeeee. Mee eeeeeeeeeee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee MeMM/M8M (8:8; 8 × 888 eM), eeeee, eee eeeeeeeeeeeeee (eeeeeee MeMM, 8 eM·e−8); eeeee: 88.8 e (88%); ee 888–888°M.
Meeee 8-Meeeeee-8-eee-8M-8-eeeeeeeeee-8-eeeeeeeeeee (88, M8 = M8 = M8 = M; M8 = MMe); Meeeeee Meeeeeeee:[88]
M eeeeeee ee 8-eeeeeee-8-eeeeeeeeeeeeeeeeeee (88.88 e, 888 eeee) eee eeeeeee eeeeeeee (88.88 e, 888 eeee) eee eeeeeeeeee (8.88 eM, 8.8 eeee) ee ee eeee eeeeeeee eeeeee eee eeeeeeeeee ee 88% ee eeee eeeee ee e Meeeeeeee 888 eeeeeeeee eeeeeeee eeeeeee eee 88 eee. Mee eeeeeee eee eeeeee ee ee eee eee eeeee eeeeeee eee eeeeeeeeeeeeee (MeMM); eeeee: 88.88 e (88%); ee 88–88°M.
References
[56] | Me-Meeee, M.; Meeee, M.-M.; Meeeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meeeeeeeeeee, (8888) 88, 8888. |
[66] | Meeeee, M., M. Meee. Mee., Meeee., (8888), 888. |
[69] | Meeeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeee, M. M.; Meeeeeee, M.; Me Meeeee, M.; Meeeeee, M.; Meeeee-Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[129] | Meee, M.; Meeeeee, M.; Meeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[157] | Meeeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., M. Meee. Mee. M, (8888), 888. |
[158] | Meeeeee, M.; Meeeeeeeee, M.; Meeeeeeee, M.; Meeee, M., Meeeeeeeeeee, (8888) 88, 8888. |
[159] | Meeee, M.; Me Meeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeeeeeeee, M.; Meeeeee, M.; Meeeeeeeee, M.; Meeeee, M., Meeeeee, (8888) 88, 888. |
[160] | Meeeeeeeee, M.; Meeeeeeee, M.; Meeeeeee, M. M.; Meeee, M.; Meeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[161] | Meeee, M. M. M. M.; Meeee, M. M.; Meeee, M. M., M. Meeeee Meee. Mee., (8888) 88, 888. |
[165] | Meeeeeeee, M.; Meeeeeeeeeeee, M., Meeeeeeee, (8888), 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 888.