- A modified Mannich reaction using 1,3-dioxolane
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Mannich reaction of ketones using 1,3-dioxolane instead of formaldehyde, paraformaldehyde, or 1,3,5-trioxane afforded the corresponding Mannich bases in high yields. Under the same conditions the aminomethylation of aromatics did not proceed but the intramolecular aminomethylation, like a Pictet-Spengler type reaction, proceeded smoothly.
- Sumita,Koumori,Ohno
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p. 1676 - 1678
(2007/10/02)
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- Synthesis of conformationally restricted relatives of the mevinic acids
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Condensations between the tricyclic ketones 9, 19 and 23 and the sodio-lithio dianion of methyl acetoacetate lead to the conformationally restricted Mevinic acid relatives 12b, 20b and 26 respectively, following lactonization and selective reduction. The approach of the nucleophile is stereospecific in the first two instances but not in the last; explanations for this behaviour are given. The target compounds showed negligible HMGCoA reductase antagonism.
- Bennett, Frank,Fenton, Garry,Knight, David W.
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p. 5147 - 5158
(2007/10/02)
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- Analgesic and tranquilizing activity of 5,8 disubstituted 1 tetralone Mannich bases
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5,8-Disubstituted 1-tetralone Mannich bases represent semirigid variants of classical (i.e., chlorpromazine) neuroleptic agents. 8-Chloro-5-methoxy-2- morpholinomethyl-1-tetralone exhibits neuroleptic potency in the thiothixene range in animal models. Of greater potential interest, however, is the analgesic potency of the 8-chloro-5-methoxy-2-pyrrolidinomethyl analogue which was in the morphine range. This compound did not induce tolerance nor was its activity reversed by naloxone. Structure-activity relationships of the series are discussed.
- Welch,Harbert,Sarges,Stratten,Weissman
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p. 699 - 705
(2007/10/04)
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