Formation of lactams and other amides under mild conditions by a

Details Formation of lactams and other amides under mild conditions by a Formation of lactams and other amides under mild conditions by a

1986-12-02

1990-07-31

Lone, Werren B.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540217, 540229, 540230, 540316, 546216, 546261, 548450, 564133, 435188, 435 45, 435 50, C07D50106, C07D49910, C07D213127, C07C10204

Patent

active

049451596

ABSTRACT:
A method for the formation of intramolecular amide bonds by the action of cyanogen, under mild reaction conditions, in the preparation of cyclic amides, including lactams, in biologically active compounds. A compound containing at least one carboxylic acid group and at least one primary or secondary amino group is reacted with cyanogen to form an intramolecular amide bond. The method has utility in the synthesis of B-lactam antibiotics, such as penicillins, cephalosporins, and their derivatives, in enzyme modification, in cyclization of peptides, and in covalent cross-linking of proteins.

REFERENCES:
patent: 3161634 (1964-12-01), Andersen
patent: 4179557 (1979-12-01), Ishimaru et al.
Kirley et al, FEBS Letters, vol. 193, No. 2, pp. 145-149, (Dec. 6, 1985).
Kirley et al, Biochemical and Biophysical Research Communications, vol. 126, No. 1, pp. 457-463, (Jan. 16, 1985).

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