Methacrylamide

Wiley, Richard H.; Waddey, Walter E.

doi:10.1002/0471264180.os029.20

Cited by 1 publication

(2 citation statements)

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“…It is important to note that 2 was obtained through a catalytic process from 1a, which is easily available from commercial sources. So far, compound 2 was prepared from malic acid by several methods, [4,5] but most reactions require the use of very strong acids such as fuming sulfuric acid, and the yield of 2 was moderate (65-75 %). Therefore, this method provides a very simple route to 2.…”

Section: Resultsmentioning

confidence: 99%

“…The most frequently used method is based on the condensation of malic acid by strong acids like fuming sulfuric acid. [5] Kvita reported an alternative method for preparing ethyl coumalate through Claisen condensation of diethyl 2-pentadioate followed by cyclization under the influence of formic acid. [6] However, the yields of the desired compounds by these methods were moderate.…”

Section: Introductionmentioning

confidence: 99%

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Selective Cyclodimerization and Cyclotrimerization of Acetals Bearing Electron‐Withdrawing Groups Catalyzed by Lewis Acids

2009

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Acetals like 3,3‐diethoxypropionate bearing electron‐withdrawing groups were found to undergo cyclodimerization and cyclotrimerization in the presence of Lewis acids to give coumalates and 1,3,5‐trisubstituted benzenes. The selectivity of these products depended on the Lewis acids employed. For instance, ethyl coumalate was obtained from ethyl 3,3‐diethoxypropionate in high selectivity under the influence of d‐block Lewis acids like FeCl3, whereas triethyl 1,3,5‐benzenetricarboxylate was obtained in preference to ethyl coumalate under the influence of lanthanoid Lewis acids like GdCl3. Various coumalates were synthesized by the FeCl3‐catalyzed cross‐cyclodimerization of acetals with active methylene compounds. From 4,4‐dimethoxy‐2‐butanone, however, 1,3,5‐triacetylbenzene, which is difficult to prepare regioselectively by conventional methods, was formed in quantitative yield under the influence of AlCl3. This reaction would provide a very convenient route to 1,3,5‐triacetylbenzene. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%