ASYMMETRIC SYNTHESIS OF OXINDOLES USING A THREE COMPONENT REACTIONVIA 1: 3 DIPOLAR CYCLOADDITION REACTION

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TAGHIZADEH MOHAMMAD JAVAD; JADIDI KHOSROW; JAVIDAN ABDOLLAH

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Seminar Paper

Paper Information

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

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Title

ASYMMETRIC SYNTHESIS OF OXINDOLES USING A THREE COMPONENT REACTIONVIA 1: 3 DIPOLAR CYCLOADDITION REACTION

Author(s)

TAGHIZADEH MOHAMMAD JAVAD | JADIDI KHOSROW | JAVIDAN ABDOLLAH

Keywords

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Abstract

1, 3-DIPOLAR CYCLOADDITION OF AZOMETHINE YLIDES IS A POWEFULL METHOD FOR THE SYNTHESIS OF HIGHLY FUNCTIONALISED FIVE-MEMBERED RING HETEROCYCLES. SOME SPIROPYRROLIDINES ARE POTENTIAL AS ANTILEUKEMIC AND ANTICONVULSANT AGENTS AND POSSESS ANTIVIRAL AND LOCAL ANAESTHETIC ACTIVITIES. IN THIS REPORT, AT FIRST WE PREPARED CHIRAL NON-RACEMIC DIPOLAROPHILES FROM THE REACTION OF ACRYLATES WITH PURE OXAZOLIDINONE AS ACHIRAL AUXILIARY. THEN THE REACTIONS WERE CARRIED OUT IN A ONEPOT AND PROCEEDED THROUGH A 1, 3-DIPOLAR CYCLOADDITION REACTION OF THE CHIRAL DIPOLAROPHILES WITH NON-STABILIZED AZOMETHINE YLIDES GENERATEDIN SITU BY THE CONDENSATION REACTION OF ISATINS WITH LPROLINE.AFTER REMOVAL OF OXAZOLIDINONE THE NEW CHIRAL SPIRO OXINDOLO- PYRROLIZIDINES WERE OBTAINED IN HIGH YIELD AND ENANTIOMERIC EXCESS. THE CONFIGURATION OF ONE OF THE CYCLOADDITION PRODUCTS CONFIRMED BY X-RAY SINGLE CRYSTAL, AND THEORETICAL CALCULATIONS.

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APA: Copy

TAGHIZADEH, MOHAMMAD JAVAD, JADIDI, KHOSROW, & JAVIDAN, ABDOLLAH. (2012). ASYMMETRIC SYNTHESIS OF OXINDOLES USING A THREE COMPONENT REACTIONVIA 1: 3 DIPOLAR CYCLOADDITION REACTION. IRANIAN SEMINAR OF ORGANIC CHEMISTRY. SID. https://sid.ir/paper/909485/en

Vancouver: Copy

TAGHIZADEH MOHAMMAD JAVAD, JADIDI KHOSROW, JAVIDAN ABDOLLAH. ASYMMETRIC SYNTHESIS OF OXINDOLES USING A THREE COMPONENT REACTIONVIA 1: 3 DIPOLAR CYCLOADDITION REACTION. 2012. Available from: https://sid.ir/paper/909485/en

IEEE: Copy

MOHAMMAD JAVAD TAGHIZADEH, KHOSROW JADIDI, and ABDOLLAH JAVIDAN, “ASYMMETRIC SYNTHESIS OF OXINDOLES USING A THREE COMPONENT REACTIONVIA 1: 3 DIPOLAR CYCLOADDITION REACTION,” presented at the IRANIAN SEMINAR OF ORGANIC CHEMISTRY. 2012, [Online]. Available: https://sid.ir/paper/909485/en

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