ONE-POT, THREE COMPONENT REACTIONS BETWEEN ISOCYANIDES AND DIALKYL ACETYLENEDICARBOXYLATES IN THE PRESENCE OF PHENYL ISOCYANATE: SYNTHESIS OF DIALKYL 2- (ALKYL/ARYLIMINO) -2, 5-DIHYDRO-5-OXO-1-PHENYL-1H -PYRROLE-3, 4-DICARBOXYLATE

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KHANDAN BARANI KHATEREH; MAGHSOODLOU MALEK TAHER; ELMI SHIRIN

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Seminar Paper

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Seminar: IRANIAN SEMINAR OF ORGANIC CHEMISTRY
Year:2012 | Issue:19

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Title

ONE-POT, THREE COMPONENT REACTIONS BETWEEN ISOCYANIDES AND DIALKYL ACETYLENEDICARBOXYLATES IN THE PRESENCE OF PHENYL ISOCYANATE: SYNTHESIS OF DIALKYL 2- (ALKYL/ARYLIMINO) -2, 5-DIHYDRO-5-OXO-1-PHENYL-1H -PYRROLE-3, 4-DICARBOXYLATE

Author(s)

KHANDAN BARANI KHATEREH | MAGHSOODLOU MALEK TAHER | ELMI SHIRIN

Keywords

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Abstract

PYRROLE DERIVATIVES ARE AN IMPORTANT CLASS OF HETEROCYCLES. NITROGEN HETEROCYCLES ARE OF SYNTHETIC INTEREST BECAUSE THEY CONSTITUTE AN IMPORTANT CLASS OF NATURAL AND NON-NATURAL PRODUCT, MANY OF WHICH EXHIBIT USEFUL BIOLOGICAL ACTIVITY. ISOCYANIDE-BASED MULTICOMPONENT REACTIONS (IMCR) NOW OCCUPY A POSITION OF IMPORTANCE IN SYNTHETIC ORGANIC CHEMISTRY, MAINLY DUE TO THE CONTRIBUTIONS OF UGI AND CO-WORKERS. ORGANIC ISOCYANATES ARE POWERFUL TOOLS IN ORGANIC SYNTHESIS. GENERALLY, ISOCYANATES EASILY UNDERGO POLAR CYCLOADDITIONS WITH A LARGE VARIETY OF UNSATURATED SUBSTRATES. THE REACTIVITY OF NUCLEOPHILIC CARBENES SUCH AS ISOCYANIDES TOWARDS DIMETHYL ACETYLENEDICARBOXYLATE (DMAD) IS WELL DOCUMENTED. IN SUMMARY, WE HAVE FOUND THAT THE REACTION OF ALKYL/ARYL ISOCYANIDES WITH DIALKYL ACETYLENEDICARBOXYLATES IN THE PRESENCE OF PHENYL ISOCYANATE LEADS TO THE ONE-POT AND SIMPLE SYNTHESIS OF HIGHLY FUNCTIONALIZED 2, 5-DIHYDRO-5-OXO-1-PHENYL-1H -PYRROLE DERIVATIVES. THE STRUCTURE OF COMPOUNDS 3A-H WAS DEDUCED FROM THEIR IR, 1H NMR, 13C NMR, MASS SPECTRAL DATA AND ELEMENTAL ANALYSIS.

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APA: Copy

KHANDAN BARANI, KHATEREH, ELMI, SHIRIN. (2012). ONE-POT, THREE COMPONENT REACTIONS BETWEEN ISOCYANIDES AND DIALKYL ACETYLENEDICARBOXYLATES IN THE PRESENCE OF PHENYL ISOCYANATE: SYNTHESIS OF DIALKYL 2- (ALKYL/ARYLIMINO) -2, 5-DIHYDRO-5-OXO-1-PHENYL-1H -PYRROLE-3, 4-DICARBOXYLATE. IRANIAN SEMINAR OF ORGANIC CHEMISTRY. SID. https://sid.ir/paper/909501/en

Vancouver: Copy

KHANDAN BARANI KHATEREH, ELMI SHIRIN. ONE-POT, THREE COMPONENT REACTIONS BETWEEN ISOCYANIDES AND DIALKYL ACETYLENEDICARBOXYLATES IN THE PRESENCE OF PHENYL ISOCYANATE: SYNTHESIS OF DIALKYL 2- (ALKYL/ARYLIMINO) -2, 5-DIHYDRO-5-OXO-1-PHENYL-1H -PYRROLE-3, 4-DICARBOXYLATE. 2012. Available from: https://sid.ir/paper/909501/en

IEEE: Copy

KHATEREH KHANDAN BARANI, SHIRIN ELMI, “ONE-POT, THREE COMPONENT REACTIONS BETWEEN ISOCYANIDES AND DIALKYL ACETYLENEDICARBOXYLATES IN THE PRESENCE OF PHENYL ISOCYANATE: SYNTHESIS OF DIALKYL 2- (ALKYL/ARYLIMINO) -2, 5-DIHYDRO-5-OXO-1-PHENYL-1H -PYRROLE-3, 4-DICARBOXYLATE,” presented at the IRANIAN SEMINAR OF ORGANIC CHEMISTRY. 2012, [Online]. Available: https://sid.ir/paper/909501/en

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