Enantioselective 1,3-Dipolar Cycloaddition of Nitrile Imines to α-Substituted and α,β-Disubstituted α,β-Unsaturated Carbonyl Substrates: A Method for Synthesizing Dihydropyrazoles Bearing a Chiral Quaternary Center

2006 ◽  
Vol 348 (16-17) ◽  
pp. 2371-2375 ◽  
Author(s):  
Mukund P. Sibi ◽  
Levi M. Stanley ◽  
Takahiro Soeta
Keyword(s):  
Dipolar Cycloaddition ◽  
Quaternary Center ◽  
Nitrile Imines

ChemInform Abstract: 1,3-Dipolar Cycloaddition of Nitrile Imines with Functionalized Acetylenes: Regiocontrolled Sc(OTf)3-Catalyzed Synthesis of 4- and 5-Substituted Pyrazoles.

ChemInform ◽  
2010 ◽  
Vol 41 (3) ◽  
Author(s):  
Bianca Flavia Bonini ◽  
Mauro Comes Franchini ◽  
Denis Gentili ◽  
Erika Locatelli ◽  
Alfredo Ricci
Keyword(s):  
Dipolar Cycloaddition ◽  
Nitrile Imines ◽  
Substituted Pyrazoles

scholarly journals 1,3-Dipolar cycloaddition of isatin N,N′-cyclic azomethine imines with α,β-unsaturated aldehydes catalyzed by DBU in water

RSC Advances ◽  
2020 ◽  
Vol 10 (41) ◽  
pp. 24288-24292 ◽  
Author(s):  
Zhan-Yong Wang ◽  
Ting Yang ◽  
Rongxiang Chen ◽  
Xueji Ma ◽  
Huan Liu ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Unsaturated Aldehydes ◽  
Quaternary Center ◽  
Azomethine Imines ◽  
Green Procedure

A simple and green procedure was established by [3 + 3] cycloaddition reaction of isatin derived cyclic imine 1,3-dipoles with α,β-unsaturated aldehydes, giving spirooxindoles with aza-quaternary center in good yields and diastereoselectivities.

1,3-Dipolar cycloaddition of nitrile imines with α,β-unsaturated lactones, thiolactones and lactams: synthesis of ring-fused pyrazoles

Tetrahedron ◽  
2012 ◽  
Vol 68 (16) ◽  
pp. 3319-3328 ◽  
Author(s):  
Jay Zumbar Chandanshive ◽  
Pedro Blas González ◽  
William Tiznado ◽  
Bianca Flavia Bonini ◽  
Julio Caballero ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Nitrile Imines ◽  
Unsaturated Lactones ◽  
Fused Pyrazoles

Decarboxylative-Mediated Regioselective 1,3-Dipolar Cycloaddition for Diversity-Oriented Synthesis of Structurally exo′-Selective Spiro[oxindole-pyrrolidine-dihydrocoumarin] Hybrids

Synthesis ◽  
2020 ◽  
Author(s):  
Ying Zhou ◽  
Xiong-Wei Liu ◽  
Shun-Qin Chang ◽  
Qi-Lin Wang ◽  
Shuang Chen ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Transition State ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Diversity Oriented Synthesis ◽  
Biologically Relevant ◽  
Good Substrate ◽  
Quaternary Center ◽  
Substrate Tolerance ◽  
High Yields

A general and practical three-component regioselective 1,3-dipolar cycloaddition of 3-amino-oxindole-based azomethine ylides and coumarins has been developed. This reaction displayed good substrate tolerance and gave a diverse array of biologically relevant spiro[ox-­i­ndole-pyrrolidine-dihydrocoumarin] derivatives bearing four contiguous stereocenters including one spiro quaternary center in moderate to high yields (up to 90%) with high diastereoselectivities (up to 15:1 dr). It is based on the application of carboxylic acid activated coumarins as dienophiles followed by a decarboxylation process. The possible mechanism of the 1,3-dipolar cycloaddition is proposed via an exo′-transition state. Furthermore, this is the first example of decarboxylative-mediated regioselective 1,3-dipolar cycloaddition of 3-amino-oxindole-based azomethine ylides and coumarins.

Heterocyclic thiones and their analogs in 1,3-dipolar cycloaddition: VII. Reaction of 4-methyl-1,3-thiazole-2(3H)-thiones with nitrile imines

2007 ◽  
Vol 43 (10) ◽  
pp. 1516-1525 ◽  
Author(s):  
E. V. Budarina ◽  
T. S. Dolgushina ◽  
M. L. Petrov ◽  
N. N. Labeish ◽  
A. A. Kol’tsov ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Heterocyclic Thiones ◽  
Nitrile Imines

1,3-Dipolar Cycloaddition of Nitrile Imines with Functionalized Acetylenes: Regiocontrolled Sc(OTf)3-Catalyzed Synthesis of 4- and 5-Substituted Pyrazoles

Synlett ◽  
2009 ◽  
Vol 2009 (14) ◽  
pp. 2328-2332 ◽  
Author(s):  
Mauro Franchini ◽  
Bianca Bonini ◽  
Denis Gentili ◽  
Erika Locatelli ◽  
Alfredo Ricci
Keyword(s):  
Dipolar Cycloaddition ◽  
Nitrile Imines ◽  
Substituted Pyrazoles
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