33566-57-3Relevant articles and documents
An expeditious entry to rare tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidin-7(8H)-ones: A single-step gateway synthesis of glochidine congeners
Seo, Jeong Moo,Hassan, Ahmed H.E.,Lee, Yong Sup
supporting information, (2019/11/26)
A single-step gateway synthesis of glochidine and its congeners that possess the rare uncommon tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidine core was developed employing histamine and readily available γ-ketoesters. Key features of the developed reaction involve tandem three C–N bonds formation and concomitant annulation of two rings in one pot to access this unique and complex tricyclic structure. Exploration of the unknown bioactivity of these compounds revealed that they elicit antiproliferative activity comparable to the anticancer drug imatinib against 6 cancer cell lines.
Cross metathesis of allyl alcohols: How to suppress and how to promote double bond isomerization
Schmidt, Bernd,Hauke, Sylvia
, p. 4194 - 4206 (2013/07/05)
Under standard conditions the cross metathesis of allyl alcohols and methyl acrylate is accompanied by the formation of ketones, resulting from uncontrolled and undesired double bond isomerization. By conducting the CM in the presence of phenol, the catalyst loading and the reaction time required for quantiative conversion can be reduced, and isomerization can be suppressed. On the other hand, consecutive isomerization can be deliberately promoted by evaporating excess methyl acrylate after completing cross metathesis and by adding a base or silane as chemical triggers.
Gold and platinum catalyzed cascade reaction of propargyl acetates bearing terminal alkynes or methyl ketones
Kusakabe, Taichi,Kato, Keisuke
experimental part, p. 1511 - 1517 (2011/03/22)
A gold (III)-catalyzed cascade reaction of propargyl acetates bearing an extra terminal alkyne (1) afforded γ-keto esters 3 and lactones 4. These products should be generated through allenyl ketone intermediate B via a 1,2-acyloxy cyclization/fragmentatio
One-pot synthesis of γ-diketones, γ-keto esters, and conjugated cyclopentenones from nitroalkanes
Ballini, Roberto,Barboni, Luciano,Bosica, Giovanna,Fiorini, Dennis
, p. 2725 - 2728 (2007/10/03)
Conjugated addition of primary nitroalkanes to α,β-unsaturated ketones or α,β-unsaturated esters, in the presence of two equivalents of DBU, allows the one-pot prepration of γ-diketones or γ-keto esters, respectively. When 2-aryl-1-nitroethane derivatives
Synthesis of 13-oxo-(Z)-9-octadecenoic acid and 15-oxo-(Z)-11-icosenoic acid, arrestants of Oryzaephilus surinamensis L.
Nakajima,Okamura,Takeda,Sugawa,Tateishi,Iwasa,Baba
, p. 551 - 552 (2007/10/03)
Two arrestants of the sawtoothed grain beetle (Oryzaephilus surinamensis L.), 13-oxo-(Z)-9-octadecenoic acid and 15-oxo-(Z)-11-icosenoic acid, were synthesized for the first time by utilizing a Z-selective Wittig reaction.
A new convenient synthesis of methyl 4-oxoalkanoates
Kulinkovich,Sorokin
, p. 361 - 362 (2007/10/02)
Methyl 4-oxoalkanoates have been obtained in good yields by treatment of 1,2-dichloro-2-alken-4-ones with sodium carbonate in methanol followed by acid-catalyzed hydrolysis of the intermediate 5-alkyl-2,2-dimethoxy-2,3-dihydrofurans.
A general synthesis of (+)-γ-substituted γ-butyrolactones using a kinetic alkylation-ozonolysis procedure
Gavin,Geraghty
, p. 1351 - 1361 (2007/10/02)
A synthesis of (±)-γ-substituted γ-butyrolactones is described in which the key intermediates, γ-ketoesters, are prepared from the readily available 6-methyl-5-hepten-2-one using a kinetic alkylation-ozonolysis procedure; the method allows terminal ester and Z-alkene groups to be incorporated into the side-chain and thus can be used for the synthesis of (+)-γ-jasmolactone as well as other naturally occurring lactones.
A Novel, Two-step, Mild and Simple Synthesis of β-, γ-, and δ-Oxo Esters from ω-Nitro Esters.
Ballini, Roberto,Bosica, Giovanna
, p. 2901 - 2912 (2007/10/02)
A convenient, mild, and simple synthesis of β-, γ-, and δ-oxo esters was achieved from ω-nitro esters.A solvent-free nitroaldol reaction of the ω-nitro esters 2 with the aldehydes 1 on alumina, followed by in situ dehydration, with addition of dichloromethane and warming gave the conjugated nitroalkenes 3, which can be converted into the carbonyl derivatives 4 by sodium hypophosphite.
Hydroacylation of Alkyl Vinyl Ketones and Acrylic Esters Using Organotetracarbonylferrates. Synthesis of 1,4-Dicarbonyl Compounds
Yamashita, Masakazu,Tashika, Haruyoshi,Uchida, Masaya
, p. 1257 - 1261 (2007/10/02)
Alkyl vinyl ketones and acrylic esters were hydroacylated with organotetracarbonylferrates to the corresponding 1,4-diketones and 4-oxo carboxylic acid derivatives in good yield in dipolar aprotic solvents such as N,N-dimethylacetamide.Addition of 18-crown-6 improved the yield. cis-Jasmone and γ-jasmolactone were synthesized by use of these reactions.
