Scope and limitations of an efficient four-component reaction for dihydropyridin-2-ones

Journal of Organic Chemistry

Volumn 75, Issue 5, 2010, Pages 1723-1732

  Scheffelaar, Rachel ^a   Parayidino, Monica ^a   Znabet, Anass ^a   Schmitz, Rob F ^a   De Kanter, Frans J J ^a   Lutz, Martin ^b   Spek, Anthony L ^b   Guerra, Célia Fonseca ^a   Bickelhaupt, F Matthias ^a   Groen, Marinus B ^a   Ruijter, Eelco ^a   Orru, Romano V A ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CIS ISOMERS; COMPUTATIONAL STUDIES; CYCLOCONDENSATION; DIASTEREO-SELECTIVITY; DIASTEREOMERIC RATIOS; DIASTEREOMERS; ELEVATED TEMPERATURE; FUNCTIONALIZED; HIGH YIELD; IN-SITU; ISONITRILES; PHOSPHONATES;

ALDEHYDES; CYANIDES; ESTERIFICATION; ESTERS; HYDROCARBONS;

REACTION INTERMEDIATES;

1 AZADIENE; 3,4 DIHYDROPYRIDINE 2 ONE DERIVATIVE; ACETIC ACID DERIVATIVE; ALDEHYDE; ALKADIENE; DIHYDROPYRIDINE 2 ONE DERIVATIVE; DIHYDROPYRIDINE DERIVATIVE; ESTER; ISOCYANOACETATE DERIVATIVE; ISONITRILE DERIVATIVE; MOLECULAR SCAFFOLD; NITRILE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CIS ISOMER; CONTROLLED STUDY; CYCLOCONDENSATION; DIASTEREOISOMER; FOUR COMPONENT REACTION; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; CYCLIZATION; ESTERS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRILES; PYRIDONES; STEREOISOMERISM;

EID: 77949304343     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902613j     Document Type: Article

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74. Although the stereochemistry of DHP-2-one 35b was not determined using NOE experiments, it is expected to have the same cis-diastereoselectivity as the DHP-2-ones prepared with α-aryl isocyanoacetates. The coupling constant between H4 and H5 is 4.4 Hz, which is similar to its isonitrile variant (4.5 Hz). In addition, the chemical shift value of the H4 proton is identical (4.34 vs 4.32 ppm).
75. A table with these values is presented in the Supporting Information. In addition to the mentioned α-acidic esters, the same parameters are calculated for 11c and 34a.
76. 13C NMR are denoted where possible.