| Abstract: | Enamines 8a-e could be chlorinated by equimolar amounts of N-chlorosuccinimide (9) generating monochloroenamines 10a-e; 10a and 10d were isolated as pure substances. Two equivalents of 9 afforded the dichloroenamines 12a,c from 8a,c. Interaction of the chlorinated enamines 10a-e and 12a,c with cyanide gave morpholino-azabicyclohexane derivatives. 10a-d, thereby, led to exo-cyano-isomers lla-c; 12a,c generated endo-cyano compounds 13a,c. In the case of the ethoxycarbonylated chloroenamine 10e a mixture of diastereomeric products 11e and 14e resulted from the analogous reaction. Reduction of 11a and 14e with lithium aluminum hydride produced a pair of diastereomeric triamines 15 and 16. A tricyclic diazasystem 19 was formed from the reaction of cyanide with the carbamoylated chloroenamine 18. Monochloroenamine 10a and dichloroenamine 12a showed a significant mutagenic behaviour in the Ames test. |
