108350-22-7Relevant articles and documents
General and Versatile Synthetic Method of Formylacetic Esters
Sato, Masayuki,Yoneda, Naoki,Katagiri, Nobuya,Watanabe, Hiroshi,Kaneko, Chikara
, p. 672 - 674 (1986)
A convenient and large scale preparation of formylacetates 4 by the reaction of alcohols with formylketene (2), readily generated in situ from formyl Meldrum's acid 1, is described.
Carlactone-type strigolactones and their synthetic analogues as inducers of hyphal branching in arbuscular mycorrhizal fungi
Mori, Narumi,Nishiuma, Kenta,Sugiyama, Takuya,Hayashi, Hideo,Akiyama, Kohki
, p. 90 - 98 (2016)
Hyphal branching in the vicinity of host roots is a host recognition response of arbuscular mycorrhizal fungi. This morphological event is elicited by strigolactones. Strigolactones are carotenoid-derived terpenoids that are synthesized from carlactone and its oxidized derivatives. To test the possibility that carlactone and its oxidized derivatives might act as host-derived precolonization signals in arbuscular mycorrhizal symbiosis, carlactone, carlactonoic acid, and methyl carlactonoate as well as monohydroxycarlactones, 4-, 18-, and 19-hydroxycarlactones, were synthesized chemically and evaluated for hyphal branching-inducing activity in germinating spores of the arbuscular mycorrhizal fungus Gigaspora margarita. Hyphal branching activity was found to correlate with the degree of oxidation at C-19 methyl. Carlactone was only weakly active (100?ng/disc), whereas carlactonoic acid showed comparable activity to the natural canonical strigolactones such as strigol and sorgomol (100?pg/disc). Hydroxylation at either C-4 or C-18 did not significantly affect the activity. A series of carlactone analogues, named AD ester and AA'D diester, was synthesized by reacting formyl Meldrum's acid with benzyl, cyclohexylmethyl, and cyclogeranyl alcohols (the A-ring part), followed by coupling of the potassium enolates of the resulting formylacetic esters with the D-ring butenolide. AD ester analogues exhibited moderate activity (1?ng–100?pg/disc), while AA'D diester analogues having cyclohexylmethyl and cyclogeranyl groups were highly active on the AM fungus (10?pg/disc). These results indicate that the oxidation of methyl to carboxyl at C-19 in carlactone is a prerequisite but BC-ring formation is not essential to show hyphal branching activity comparable to that of canonical strigolactones.
A convenient synthesis of indole-substituted 2-pyrrolidones and their cyclized derivatives
Boisbrun, Michel,Jeannin, Laurent,Toupet, Loic,Laronze, Jean-Yves
, p. 3051 - 3057 (2007/10/03)
Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, dependi
SYNTHESIS OF 1,3-DIOXIN-4-ONES AND THEIR USE IN SYNTHESIS. XVI. 4-OXO-1,3-DIOXIN-5-CARBOXYLIC ACIDS AND RELATED COMPOUNDS: VERSATILE INTERMEDIATES FOR THE SYNTHESIS OF 6-UNSUBSTITUTED SIX-MEMBERED HETEROCYCLIC COMPOUNDS
Sato, Masayuki,Katagiri, Nobuya,Takayama, Kazuhisa,Hirose, Masatoshi,Kaneko, Chikara
, p. 665 - 669 (2007/10/02)
A novel method for the synthesis of so far unknown 1,3-dioxin-4-ones having a carboxyl group at the 5-position is described.Reaction of formyl Meldrum's acid and an alcohol in an aprotic solvent at 50-60 deg C gave the corresponding half esters of formylmalonic acid.Treatment of the latter with appropriate ketones in acetic anhydride containing a catalytic amount of p-toluenesulfonic acid gave the desired dioxinone-5-carboxylates.Successful conversion of these 1,3-dioxin-4-ones either to 1,3-oxazine-2,4-dione or uracil derivatives having an alkoxycarbonyl group at the 5-position demonstrated that these dioxinones can serve as chemical equivalents for alkoxycarbonylformylketenes.The fact that 5-benzyloxycarbonyl-1,3-dioxin-4-one can readily be transformed to the so far unknown 5-aminodioxinone derivative indicates further the importance of the dioxinone having a carboxyl group at the 5-position as a new building block for heterocyclic compounds.Keywords: 4-oxo-1,3-dioxin-5-carboxylic acid; formylmalonic acid half ester; Meldrum's acid; 5-amino-1,3-dioxin-4-one; cycloaddition; 4-oxo-1,3-oxazine-5-carboxylate; 2-dimethylamino-1,3-oxazin-4-one; alkoxycarbonylformylketene
