scholarly journals 5-(Methylthio)tetrazoles as versatile synthons in the stereoselective synthesis of polycyclic pyrazolines via photoinduced intramolecular nitrile imine–alkene 1,3-dipolar cycloaddition

2014 ◽  
Vol 5 (6) ◽  
pp. 2407-2415 ◽  
Author(s):  
Daniel Pla ◽  
Derek S. Tan ◽  
David Y. Gin
Keyword(s):  
Stereoselective Synthesis ◽  
Dipolar Cycloaddition ◽  
Nitrile Imine

A versatile thioether substituent on tetrazoles enables facile photoinduced intramolecular nitrile imine cycloadditions to form polycyclic pyrazolines.

π-Facial Selectivity in 1,3-Dipolar Cycloaddition Reactions of α-Methylidene-γ-lactone Substituted by 4-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl Group in γ-Position

2002 ◽  
Vol 67 (3) ◽  
pp. 353-364 ◽  
Author(s):  
Petr Melša ◽  
Ctibor Mazal
Keyword(s):  
Double Bond ◽  
Carboxylic Acid ◽  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Enantiomerically Pure ◽  
Nitrile Imine ◽  
Facial Selectivity ◽  
Excellent Selectivity

Diastereoselectivity of 1,3-dipolar cycloaddition reactions of benzyl azide, diazomethane, a nitrile oxide and a nitrile imine to α-methylidene-γ-lactone dipolarophile was effectively controlled by a bulky γ-substituent, 4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl in γ-position of the dipolarophile. The dipoles added from the less hindered face of the double bond with an excellent selectivity. Enantiomerically pure dipolarophile was prepared from the easily available (S)-5-oxotetrahydrohydrofuran-2-carboxylic acid.

1,3-Dipolar Cycloaddition of Isatin-Derived Azomethine Ylides with 2H-Azirines: Stereoselective Synthesis of 1,3-Diazaspiro[bicyclo[3.1.0]hexane]oxindoles

2019 ◽  
Vol 84 (7) ◽  
pp. 4273-4281 ◽  
Author(s):  
Anikó Angyal ◽  
András Demjén ◽  
Veronika Harmat ◽  
János Wölfling ◽  
László G. Puskás ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition

Stereoselective synthesis of dispiro heterocycles by [3 + 2] cycloaddition of azomethine ylides with a thiazolo[3,2-a]indole derivative

2020 ◽  
Vol 18 (39) ◽  
pp. 7822-7826
Author(s):  
Vidya Sathi ◽  
Noble V. Thomas ◽  
Ani Deepthi
Keyword(s):  
Green Synthesis ◽  
Indole Derivative ◽  
Stereoselective Synthesis ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition

Green synthesis of dispiro oxindole heterocycles by 1,3-dipolar cycloaddition of isatin-derived azomethine ylides with a dipolarophile derived from thieno[2,3-b]indole-2,3-dione.

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