Beilstein J. Org. Chem.2024,20, 280–286, doi:10.3762/bjoc.20.29
developed by means of [4 + 2] annulation reaction of 3-substituted benzoisothiazole 1,1-dioxides with 1,2-diaza-1,3-dienes. This approach displays advantages such as mild reaction conditions, wide substrate range tolerance, simple operation, compatibility with gram-scale preparation.
Keywords: [4 + 2
] annulation reaction; 1,2-diaza-1,3-dienes; spiro-benzosultams; 3-substituted benzoisothiazole 1,1-dioxides; Introduction
Spirobenzosultams have various biological activities [1][2][3] such as antiviral, anticancer, antimicrobial, antimalarial, and antileukemia, and are widely used in the pharmaceutical
ketimines as suitable three-carbon synthons in [3 + 2] and [3 + 3] annulations [11][12][13][14][15]. However, methods using N-sulfonyl ketimines as dienophiles in [4 + 2] annulation reactions to afford biologically important spiro compounds are still limited to date [16]. 1,2-Diaza-1,3-dienes [17][18][19
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Graphical Abstract
Scheme 1:
Comparision of previous work with this work.
Beilstein J. Org. Chem.2016,12, 1269–1301, doi:10.3762/bjoc.12.121
4:1 in the presence of 4 Å molecular sieves (Scheme 59) [97].
A sequential three-component enamine–azoene annulation reaction of primary aliphatic amines 292, activated methylene compounds 293, and 1,2-diaza-1,3-dienes (DDs, 294) has been reported to give polysubstituted pyrroles 295 (Scheme 60) [98