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US 6,476,236 B1Granted
Synthesis of 2-cyanoaziridine-1-carboxamide
AssigneeArizona Board of Regents
InventorsWilliam Remers, Bashyam Iyengar
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Abstract
The present invention provides a process for producing an aziridine-1-carboxamide of the formula: from an aziridine of the formula: and an isocyanate of the formula R5—N═C═O, where R1, R2, R3, R4 and R5 are those defined herein. In addition, the present invention also provides a process for producing a 4-imino-1,3-diazabicyclo[3.1.0]-hexan-2-one of the formula: from the aziridine-1-carboxamide of Formula I.
Claims5
A process for producing an aziridine-1-carboxamide of the formula:
- said process comprising:
- (a) contacting an aziridine of the formula:
- with an isocyanate of the formula R5—N═C═O under conditions sufficient to produce an N-acylated aziridine of the formula:
- wherein
- each of R1, R2 and R3 is independently hydrogen or C1-C6 alkyl;
- R4 is cyano, carboxamide or carboxylic acid ester;
- and
- R5 is a moiety of the formula —C(═O)—R6, where R6 is haloalkyl, and
- (b) removing the R5 group by contacting the N-acylated aziridine with a nucleophilic reagent under conditions sufficient to produce the aziridine-1-carboxamide of Formula I.
6 more elements
Dependencies are inferred from the claim text.