Chlorosulfonyl Isocyanate

Miller, Marvin J.; Ghosh, Manuka; Guzzo, Peter R.; Vogt, Paul F.; Hu, Jingdan; Filzen, Gary F.; Geyer, Andrew

doi:10.1002/047084289x.rc149.pub2

Encyclopedia of Reagents for Organic Synthesis 2005

DOI: 10.1002/047084289x.rc149.pub2

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Chlorosulfonyl Isocyanate

Marvin J. Miller¹,

Manuka Ghosh²,

Peter R. Guzzo³

et al.

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2024

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Application of Chlorosulfonyl Isocyanate (CSI) in the Synthesis of Fused Tetracyclic Ketone Ring Systems

VanNatta,

Niu,

Carlson

et al. 2024

J. Org. Chem.

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Chlorosulfonyl isocyanate (CSI) is a complex reagent capable of facilitating numerous synthetic transformations, including lactam/lactone formation, sulfonylation, Friedel–Crafts-type acylations, and cycloadditions. Annulation reactions to form nitrogen-, oxygen-, and sulfur-bearing heterocycles have been observed with CSI; however, the application of CSI toward the generation of fused cyclic ketone ring systems has not been previously reported. A serendipitous discovery of the pertinence of CSI occurred during a structure–activity relationship campaign around our established lead benzosuberene-based molecule that functions as a potent inhibitor of tubulin polymerization. The benzylic olefin within this molecule represents a promising moiety for further functionalization. CSI was initially investigated as a reagent to effect transformation of this olefin to its corresponding β-lactam functionality, but instead resulted in an unexpected tetracyclic fused ring system in high yield (88%). This finding led to an exploration of the reactivity of CSI with various arenes. Benzosuberene analogues with varying functionalizations were synthesized and treated with CSI, with all examples resulting in a fused ring system except those bearing electron-withdrawing groups. Notably, simplified arene structures with fewer substituents were also observed to undergo cyclization under these conditions. This strategy represents a promising approach for the synthesis of appropriately functionalized tetracyclic ring systems.

show abstract

Application of Chlorosulfonyl Isocyanate (CSI) in the Synthesis of Fused Tetracyclic Ketone Ring Systems

VanNatta,

Niu,

Carlson

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

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Chlorosulfonyl Isocyanate

Cited by 1 publication

References 87 publications

Application of Chlorosulfonyl Isocyanate (CSI) in the Synthesis of Fused Tetracyclic Ketone Ring Systems

Application of Chlorosulfonyl Isocyanate (CSI) in the Synthesis of Fused Tetracyclic Ketone Ring Systems

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