92449-52-0Relevant articles and documents
Diazo reagents in copper(I)-catalyzed olefination of aldehydes
Lebel, Helene,Davi, Michael
supporting information; experimental part, p. 2352 - 2358 (2009/10/02)
The olefination of aldehydes to synthesize unsaturated ketones, esters, amides and phosphonates using diazo reagents and triphenylphosphine in the presence of copper(I) iodide as catalyst, is described. Good to excellent E:Z selectivities as well as yields were obtained for a large variety of aliphatic, aromatic and heteroaromatic aldehydes. The reaction showed also an excellent functional group compatibility and aldehydes were selectively reacted in the presence of ketone, nitro, amine, ether, acetal, thioether and halide groups. The use of a cost-effective copper salt as a catalyst is advantageous compared to previously reported expensive transition metal complexes. The method was used in the total synthesis of the scutifoliamide A, a biologically active compound that exhibits antifungal activity.
Esters and amides from activated alcohols using manganese(IV) dioxide: Tandem oxidation processes
Foot, Jonathan S.,Kanno, Hisashi,Giblin, Gerard M. P.,Taylor, Richard J. K.
, p. 1055 - 1064 (2007/10/03)
Manganese(IV) dioxide can be used in conjunction with sodium cyanide in THF-methanol or in methanol alone for the direct conversion of activated alcohols into methyl esters. Ethyl and isopropyl esters can also be prepared. Similarly, use of manganese(IV) dioxide and sodium cyanide in THF containing ammonia or primary amines can be used to convert alcohols into the corresponding amides. Several activated alcohols and one non-activated alcohol example are reported.
Michael Addition of Malononitrile to α-Acetylcinnamamides
Martin, Nazario,Martinez-Grau, Angeles,Seoane, Carlos,Marco, Jose L.,Albert, Armando,Cano, Felix H.
, p. 801 - 804 (2007/10/02)
The reaction of α-acetylcinnamamides 7a-e with malononitrile using piperidine as the catalyst is described.When one or two equivalents of malononitrile are used, the 2-amino-4H-pyran 6a or the polyfunctionalized carbocycles 9b-e, respectively, can be isolated as major products, depending on the experimental conditions.Compounds 9b-e apparently arise from a sequential Michael plus Knoevenagel addition of two molecules of malononitrile followed by Thorpe cyclization.The structure of 9b was determined by an X-ray crystallographic analysis, which revealed a twisted cyclohexadiene ring with characteristic crystal packing.Key Words: Cinnamamides, α-acetyl / Malononitrile / 4H-Pyrans / Michael additions
Stereoselective Synthesis of (2E)-, (2E,4E)-Unsaturated Carboxamides via Tellurium Ylides
Huang, Zhi-Zhen,Wen, Liang-Wei,Huang, Xian
, p. 2579 - 2584 (2007/10/02)
Reaction of dibutyl(alkylcarbamoylmethyl)tellurium halides with aldehydes in presence of potassium carbonate gave α,β-unsaturated carboxamides with high E-selectivity and good yields.
HOMOLYTIC AZIRIDINE OPENING (AZA VARIANT OF CYCLOPROPYLCARBINYL-HOMOALLYL REARRANGEMENT) BY ADDITION OF TRIBUTYLTIN RADICAL TO N-ACYLAZIRIDINES. FACTORS CONTRIBUTING TO THE REGIOSELECTIVITY
Werry, Juergen,Stamm, Helmut,Lin, Pen-Yuan,Falkenstein, Reinhard,Gries, Stefan,Irngartinger, Hermann
, p. 5015 - 5028 (2007/10/02)
AIBN initiated reaction of N-acylaziridines 1 with Bu3SnH in refluxing benzene provided products 5 and 8 of reductive ring opening.Yields (practically quantitative in most cases) fell drastically with steric hindrance of the addition of Bu3Sn to the acyl oxygen of 1.They depended to some extent on the experimental conditions for hydrogen capturing when aziridine homolysis provided a primary radical 3 or 6.The regioselectivity of (probably reversible) ring homolysis can be understood in terms of the stability of the arising radical (3, 6), of stereoelectronic control (e.g. 1i as compared to 1h) and of frontier orbital interactions (1j).A possible difference in bond lengths as explanation for the formation of the primary radical from 1j did not find support from an X-ray structure analysis of N-tosyl-2-methyl-aziridine 11.Isomeric products were obtained only twice (1i, 1j) with a dependence of the ratio 5j:8j on concentration and hydrogen isotope of Bu3SnH.No such dependence was found for the ratio 5:14 (reduction without and with an intervening cyclization of 3 leading to a pyrrolidone) obtained from the N-cinnamoylaziridine 1l.This ratio (1:9 for 1l and 1:3 for 1n) must reflect the E-Z isomers in 3.The observed preference for the formation of E-3 from 2 can be explained by stereoelectronic and steric effects.A cinnamoyl double bond in 5 was saturated depending on experimental conditions.
A GENERAL AND HIGHLY STEREOSELECTIVE APPROACH TO UNSATURATED ISOBUTYLAMIDES VIA ARSONIUM SALT. NEW SYNTHESIS OF PELLITORINE
Shi, Lilan,Yang,, Jianhua,Wen, Xueging,Huang, Yao-Zeng
, p. 3949 - 3950 (2007/10/02)
The highly stereoselective synthesis of conjugated unsaturated isobutylamides in good yields via the arsonium salt is described, and the new synthesis of pellitorine is also reported.
A CONVENIENT METHOD FOR THE SYNTHESIS OF αβ-UNSATURATED CARBOXYLIC ACID AMIDES UTILIZING A NEW HETERO-BIFUNCTIONAL REAGENT, DMPATT
Nagao, Yoshimitsu,Hagiwara, Yuichi,Yamada, Shozo,Ochiai, Masahito,Fujita, Eiichi
, p. 4686 - 4689 (2007/10/02)
As a new extention of monitored aminolysis of 3-acyl-1,3-thiazolidine-2-thione(ATT), a convenient procedure for the synthesis of αβ-unsaturated carboxylic acid amides has been developed using a new hetero-bifunctional reagent, 3-dimethylphosphonoacetyl-1,3-thiazolidine-2-thione (DMPATT).DMPATT was effectively used as the bridging reagent between amino (or imino) compounds and aldehydes (or ketone) to afford various olefinic amides in good yields.KEYWORDS - thiazolidine-2-thione; hetero-bifunctional reagent; αβ-unsaturated amide; Wittig reaction; ferulyltryptamine
