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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1070382Generated: October 26, 2026

Furan → (3,5-Dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-4-yl)acetonitrile

https://huagongshe.com/reaction/1070382

Reaction equation

Participants

RoleNameHCIDCharge
ReactantFuranHCID 8029—
ReactantMaleimideHCID 10935—
ReactantBromoacetonitrileHCID 11534—
Reactant10-Oxa-4-azatricyclo(5.2.1.02,6)decane-3,5-dioneHCID 239727—
SolventAcetoneHCID 180—
SolventDimethylformamideHCID 6228—
Product(3,5-Dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-4-yl)acetonitrileHCID 22396537—

Reaction Steps

Synthesis took place in analogy to Example VI a from 10-oxa-4-azatricyclo[5.2.1.02,6]decane-3,5-dione (obtainable from maleimide and furan from Diels-Alder reaction for example as described by Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T.; J Org Chem 1997, 62, 4088-4096 and subsequent hydrogenation as described by Ansell, M. F.; Caton, M. P. L.; North, P. C.; Tetrahedron Lett. 1982, 23, 2811) and bromoacetonitrile with the exception that acetone was used as solvent in place of DMF. The substance was employed as crude product in the next reaction.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06903089B1
Source datasetuspto-grants-2005_06
ORD IDord-5397b9d01bdc473a8cd5f7b98554a071
Source noteuspto-grants-2005_06