Process for the production of lactams

Details Process for the production of lactams Process for the production of lactams

Filed on

1992-09-03

Date issued

1994-04-05

Examiner

Rotman, Alan L.

Patent Class

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

SubClass

Organic compounds

SubSubClass

Heterocyclic carbon compounds containing a hetero ring...

Other Related Categories

546296, C07D21136

Type

Patent

Status

active

Patent number

053006496

Description

ABSTRACT:
.beta.,.gamma.-unsaturated .delta.-lactams, especially 2-azabicyclo[2.2.1]hept-5-en-3-one, are produced by Diels-Alder reaction of 1,3-dienes with sulfonyl cyanides and subsequent hydrolysis. The sulfonyl cyanides were formed in situ from cyanogen chloride and the corresponding sulfinates. By the renewed reaction of the sulfinate formed in the hydrolysis of the Diels-Alder adducts with cyanogen chloride, the sulfonyl cyanides are regenerated and a catalytic cyclic process results. The 2-azabicyclo[2.2.1]hept-5-en-3-one is a starting compound in the synthesis of antiviral nucleoside analogs.

REFERENCES:
patent: 3737457 (1973-06-01), Cox et al.
Daluge et al., Journal of Organic Chemistry, vol. 43, No. 12, (1978) pp. 2311 to 2320.
Organic Synthesis, vol. 57 (1977), pp. 88 to 92.
Tetrahedron Letters, vol. 39, (1969) pp. 3351 and 3352.
Jagt et al., J. Org. Chem., 39, (1974), pp. 564 to 566.

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