scholarly journals α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles

2019 ◽  
Vol 17 (37) ◽  
pp. 8467-8485 ◽  
Author(s):  
Abderrahman El Bouakher ◽  
Arnaud Martel ◽  
Sébastien Comesse
Keyword(s):  
Ring Closure ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions

This review presents the use of α-alkyl- and α-alkoxy-halogenoacetamides as powerful partners for domino and 1,3-dipolar cycloaddition reactions resulting in a ring closure.

scholarly journals Photochemical and thermal intramolecular 1,3-dipolar cycloaddition reactions of new o-stilbene-methylene-3-sydnones and their synthesis

2011 ◽  
Vol 7 ◽  
pp. 1663-1670 ◽  
Author(s):  
Kristina Butković ◽  
Željko Marinić ◽  
Krešimir Molčanov ◽  
Biserka Kojić-Prodić ◽  
Marija Šindler-Kulyk
Keyword(s):  
Acetic Acid ◽  
Photochemical Reactions ◽  
Acid Anhydride ◽  
Ring Closure ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Thermal Reactions

New trans- and cis-o-stilbene-methylene-sydnones 3a,b were synthesized by transforming the trans- and cis-o-aminomethylstilbene derivative, obtained by reduction of corresponding o-cyano derivatives, into glycine ester derivatives (43 and 31% yield) followed by hydrolysis (90 and 96% yield), nitrosation and ring closure with acetic acid anhydride (30 and 40% yield). The products were submitted to photochemical and thermal intramolecular [3 + 2] cycloadditions to afford diverse heteropolycyclic compounds. Photochemical reactions afforded cis-3-(4-methylphenyl)-3a,8-dihydro-3H-pyrazolo[5,1-a]isoindole (11, 12.5% yield) and trans-3-(4-methylphenyl)-3a,8-dihydro-3H-pyrazolo[5,1-a]isoindole (12, 5% yield). Thermal reactions afforded 3-(4-methylphenyl)-3,3a,8,8a-tetrahydroindeno[2,1-c]pyrazole (14, 50% yield) and 11-(4-methylphenyl)-9,10-diazatricyclo[7.2.1.02,7]dodeca-2,4,6,10-tetraene (15, 22% yield).

Multicomponent 1,3-Dipolar Cycloaddition Reactions in the Construction of Hybrid Spiroheterocycles

2013 ◽  
Vol 17 (18) ◽  
pp. 1929-1956 ◽  
Author(s):  
Natarajan Arumugam ◽  
Raju Kumar ◽  
Abdulrahman Almansour ◽  
Subbu Perumal
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions

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 cycloadditions of Arylcarbonitrile Oxides and Diaryl Nitrilimines with Some 2-Arylmethylene-1,3-Indanediones; regiochemistry of the Reactions

2003 ◽  
Vol 2003 (4) ◽  
pp. 204-207 ◽  
Author(s):  
Sarra Boudriga ◽  
Mohiedinne Askri ◽  
Rafik Gharbi ◽  
Mohamed Rammah ◽  
Kabula Ciamala
Keyword(s):  
Ring Closure ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions

Ring-closure reaction affording spiroisoxazolines and spiropyrazolines via a 1,3-dipolar cycloaddition between the title compounds, occurs with high regioselectivity.

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