Phosphorylation of cyclic amides

Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...

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540542, 540566, 540571, 540572, C07D24314, C07D48704

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047390492

ABSTRACT:
Compounds of the general formula ##STR1## are reacted with a strong base followed by a phosphorylating agent, such as dicyclicaminophosphinic halide or bis-di-lower alkylaminophosphinic halide to produce an imine of the formula ##STR2## wherein R is dicyclicaminophosphinyloxy or bis-di-lower alkylaminophosphinyloxy.
R represents a leaving group which will undergo nucleophilic displacement with nitrogen, oxygen, sulfur and carbon containing nucleophiles, that is, nucleophiles which have, as a reactive site, a nitrogen, oxygen, sulfur or carbon atom, such that, when the cyclic imine undergoes nucleophilic displacement, there is formed C--N, C--O, C--S and C--C bonds between the carbon atom of the cyclic imine and the nucleophilic group.
The end products may be utilized as intermediates in the production of pharmaceutically valuable compounds and, in some instances, are pharmaceutically valuable compounds per se.

REFERENCES:
patent: 4349477 (1982-09-01), Walser et al.
Ning et al, J. Org. Chem., vol. 41, No. 16 (1976) pp. 2720-2727.

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