1,4-Quinone Cycloaddition Reactions with Alkenes, Alkynes, and Related Compounds

2003 ◽  
Author(s):  
Andrew Gilbert
Keyword(s):  
Cycloaddition Reactions ◽  
Related Compounds

ChemInform Abstract: Cycloaddition Reactions of Oxaquadricyclane, Oxanorbornadiene, and Related Compounds with Cyclooctyne.

ChemInform ◽  
2010 ◽  
Vol 30 (24) ◽  
pp. no-no
Author(s):  
Kiyoshi Matsumoto ◽  
Hiroyuki Taketsuna ◽  
Yukio Ikemi ◽  
Akikazu Kakehi ◽  
Takane Uchida ◽  
...  
Keyword(s):  
Cycloaddition Reactions ◽  
Related Compounds

scholarly journals Reduced 3,4′-bipyrazoles carrying thiophene and thiazole substituents: structures of two intermediates and two products

2021 ◽  
Vol 77 (4) ◽  
pp. 335-340
Author(s):  
Chayanna Harish Chinthal ◽  
Hemmige S. Yathirajan ◽  
Nagaraja Manju ◽  
Balakrishna Kalluraya ◽  
Sabine Foro ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Intermolecular Interactions ◽  
Cycloaddition Reactions ◽  
Independent Components ◽  
Analogous Compound ◽  
A Chain ◽  
Related Compounds ◽  
Centrosymmetric Dimers

Cycloaddition reactions between 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(thiophen-2-yl)prop-2-en-1-ones and thiosemicarbazide leads to the formation of reduced 3,4′-bipyrazole-2-carbothioamides. Further cycloaddition of these intermediates with either diethyl acetylenedicarboxylate or 4-bromophenacyl bromide leads to reduced 3,4′-bipyrazoles carrying oxothiazole or thiazole substituents, respectively. The structures of two representative intermediates and two representative products established unambiguously the regiochemistry of the cycloaddition reactions. The molecules of 3′-methyl-5′-(2-methylphenoxy)-1′-phenyl-5-(thiophen-2-yl)-3,4-dihydro-1′H,2H-3,4′-bipyrazole-2-carbothioamide, C25H23N5OS2 (Ia), are linked by N—H...N hydrogen bonds to form simple C(8) chains. The analogous compound 5′-(2,4-dichlorophenoxy)-3′-methyl-1′-phenyl-5-(thiophen-2-yl)-3,4-dihydro-1′H,2H-3,4′-bipyrazole-2-carbothioamide hemihydrate crystallizes as a hemihydrate, C24H19Cl2N5OS2·0.5H2O (Ib), and the independent components are linked into a chain of spiro-fused R 4 4(20) rings by a combination of O—H...N and N—H...O hydrogen bonds. In the structure of ethyl (Z)-2-{2-[3′-methyl-1′-phenyl-5-(thiophen-2-yl)-5′-(2-methylphenoxy)-3,4-dihydro-1′H,2H-3,4′-bipyrazole-2-yl]-4-oxo-4,5-dihydrothiazol-5-ylidene}acetate, C31H27N5O4S2 (II), inversion-related pairs of molecules are linked by paired C—H...π(arene) hydrogen bonds to form cyclic centrosymmetric dimers, but there are no direction-specific intermolecular interactions in 4-(4-bromophenyl)-2-[5′-(2,4-dichlorophenoxy)-3′-methyl-1′-phenyl-5-(thiophen-2-yl)-3,4-dihydro-1′H,2H-3,4′-bipyrazole-2-yl]-4-thiazole, C32H22BrCl2N5OS2 (III). Comparisons are made with the structures of some related compounds.

Cycloaddition Reactions of Oxaquadricyclane, Oxanorbornadiene, and Related Compounds with Cyclooctyne

Heterocycles ◽  
1998 ◽  
Vol 49 (1) ◽  
pp. 79 ◽  
Author(s):  
Kiyoshi Matsumoto ◽  
Hiroyuki Taketsuna ◽  
Yukio Ikemi ◽  
Akikazu Kakehi ◽  
Takane Uchida ◽  
...  
Keyword(s):  
Cycloaddition Reactions ◽  
Related Compounds

Regiospecific cycloaddition reactions using functionalized isoprenylsilane and related compounds

1985 ◽  
Vol 26 (42) ◽  
pp. 5175-5178 ◽  
Author(s):  
Akira Hosomi ◽  
Yasuyuki Sakata ◽  
Hideki Sakurai
Keyword(s):  
Cycloaddition Reactions ◽  
Related Compounds
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