132338-45-5Relevant academic research and scientific papers
Enantioselective Lactonization by π-Acid-Catalyzed Allylic Substitution: A Complement to π-Allylmetal Chemistry
Aponick, Aaron,Kizhakkayil Mangadan, Arun Raj,Liu, Ji
supporting information, p. 22224 - 22229 (2021/09/09)
Asymmetric allylic alkylation (AAA) is a powerful method for the formation of highly useful, non-racemic allylic compounds. Here we present a complementary enantioselective process that generates allylic lactones via π-acid catalysis. More specifically, a
Catalytic Dehydrative Lactonization of Allylic Alcohols
Liu, Ji,Miotto, Romain J.,Segard, Julien,Erb, Ashley M.,Aponick, Aaron
supporting information, p. 3034 - 3038 (2018/05/28)
A convenient strategy for the synthesis of phthalides and ?-butyrolactones is reported. The method utilizes readily prepared allylic alcohols in formal Au(I)- and Pd(II)-catalyzed SN2′ reactions. Using these catalysts, exclusive formation of the desired five-membered lactones is observed, completely avoiding the competing direct lactonization pathway that forms the undesired seven-membered ring with protic acids and alternative metal salts. This mild and operationally simple method notably tolerates exomethylene groups and should find use in both phthalide and terpene syntheses.
Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum
Anderson, Marc O.,Sherrill, John,Madrid, Peter B.,Liou, Ally P.,Weisman, Jennifer L.,DeRisi, Joseph L.,Guy, R. Kiplin
, p. 334 - 343 (2007/10/03)
A parallel synthetic strategy to the 9-aminoacridine scaffold of the classical anti-malarial drug quinacrine (2) is presented. The method features a new route to 9-chloroacridines that utilizes triflates of salicylic acid derivatives, which are commercially available in a variety of substitution patterns. The route allows ready variation of the two diversity elements present in this class of molecules: the tricyclic aromatic heterocyclic core, and the disubstituted diamine sidechain. In this study, a library of 175 compounds was designed, although only 93 of the final products had purities acceptable for screening. Impurity was generally due to incomplete removal of 9-acridones (18), a degradation product of the 9-chloroacridine synthetic intermediates. The library was screened against two strains of Plasmodium falciparum, including a model of the drug-resistant parasite, and six novel compounds were found to have IC50 values in the low nanomolar range.
INHIBITORS OF MICROSOMAL TRIGLYCERIDE TRANSFER PROTEIN AND APO-B SECRETION
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Page/Page column 20; 24, (2008/06/13)
The present invention relates to compounds which are inhibitors of microsomal triglyceride transfer protein and/or apolipoprotein B (Apo B) secretion. These compounds can be useful for the prevention and treatment of various diseases, particularly atheros
Convergence in [2+2+2] synthesis of β-phenylnaphthalene motif in polyaromatic natural products
Takemura, Isao,Imura, Koreaki,Matsumoto, Takashi,Suzuki, Keisuke
, p. 6673 - 6676 (2007/10/03)
Two optional routes to β-phenylnaphthalene structure are developed by introducing α- and β-styryl groups onto different positions in the benzocyclobutene ring followed by ring enlargement.
Aminoalkoxybenzoyl-benzofuran or benzothiophene derivatives, method for preparing same and compositions containing same
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Page/Page column 29, (2010/02/05)
The invention relates to benzofuran or benzothiophene derivatives of general formula: 1These compounds are of use as medicinal products, in particular in the treatment of pathological syndromes of the cardiovascular system.
Aminoalkoxybenzoyl-benzofuran or benzothiophene derivatives, method of preparing same and compositions containing same
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Page 23, (2010/02/03)
Benzothiophenes and related compounds of formula (1), wherein A, B, Z are independently —CH═, —CR4═ or ═N—; X is —S—, —O—, —NH—, —NR2, —CH2—CH2—, CH2—CH2—CH2—, —CH2—O—; —OCH2—, —CH2—S—, —CO—, —SCH2—. —N═CR2— or —R2C═N—; Y is optionally substituted phenyl, alkyl, cycloalkyl, cycloalkenyl, heterocycle or bicyclic ring system; D is —CO—, CR2R3—, —CONH—, —NHCO—, —CR2(OH)—, —CONR2, NOR1 CH—NO2 N—CN —NR2—CO—, —C—, —C—, —C—; E is a single bond, optionally substituted phenyl, heterocycle; Z1 is —(CH2)p W(CH2)q—, —O(CH2)p CR5R6— or —O(CH2)p W(CH2)q; G is —NR7R8, (a), (b), (c), a 5- or 6-membered saturated, unsaturated or partially unsaturated and optionally substituted heterocycle or a bicyclic amine containing 5 to 12 carbon atoms either bridged or fused and optionally substituted and R is halogen, —NR2R3, —NHCOR2, —NHSO2R2, —CR2R3OH, —CONR2R3, —SO2NR2R3, OH, —OR1, —O—COR1; are estrogen agonists which are useful for treating syndromes and diseases caused by estrogen deficiency.
Palladium-Catalyzed Cross-Coupling Reactions of Highly Hindered, Electron-Rich Phenol Triflates and Organostannanes
Saa, Jose M.,Martorell, Gabriel,Garcia-Raso, Angel
, p. 678 - 685 (2007/10/02)
The palladium-catalyzed cross-coupling reaction of highly hindered, electron-rich phenol triflates and organostannanes (Stille reaction) has been studied in a systematic manner.The following are its salient features: (1) electron-rich phenol triflates require triphenylphosphine to undergo palladium-catalyzed cross-couplings; (2) in general, efficient reactions take place only when larger-than-usual amounts (10-15percent) of palladium are employed.On the reagent side, alkyl- (methyl only), allyl-, vinyl- and alkinylstannanes undergo efficient cross-couplings with the titlesubstrates.However, some limitations to this novel entry to 2-substituted resorcinols exist in regard to both substrates and reagents.Thus, conformationally rigid (hexasubstituted) aryl triflates behave poorly, demethylation being an important side reaction.Moreover, alkyl groups other than methyl cannot be introduced because β elimination occurs more rapidly.The potentially powerful synthesis of hindered biaryls has also been studied briefly.In the present conditions, the reaction appears to be limited by the presence of ortho substituents on the arylstannane moiety.
MOLECULES FOR INTRAMOLECULAR RECOGNITION. SYNTHESIS AND STRUCTURES OF DIARYL- AND ARYLNAPHTHYLETHYNES
Evans, Kevin L.,Prince, Philippe,Huang, Enoch T.,Boss, Keisha R.,Gandour, Richard D.
, p. 6753 - 6756 (2007/10/02)
While synthesizing models for intramolecular recognition, a simple and efficient method for forming terminal arylethynes was developed and palladium-catalyzed coupling chemistry of alkynes with either aryl iodides or aryl triflates was used to form crowde
