Nitrodisulfides on treatment with SmI2 in anhydrous THF at room temperature lead to reactive intermediates, which are “living” double-anions and react smoothly with α,β-unsaturated ketones to afford 2,3-dihydro-1,5-benzothiazepines in good yields under mild and neutral conditions.
References
1.
KrapchoJ., and YaleH. L., U.S. 3,117,124(1964) (Chem. Abstr., 8049a 60 1964).
2.
(a) NaegeleH., BehnkeB., GebbardtA., and StrohbeckM., Clin. Biochem., 1998, 31, 37; b) B.J. Materson, D.J. Reda, D.W. Williams, Am. J. Hypertens, 1998, 11, 597.
3.
De SarroG., ChimirriA., De SarroA., GittoR., GrassoS., and ZapalaM., Eur. J. Med. Chem., 1995, 30, 925.
4.
(a) RiedW., MarkW., Chem. Ber., 1957, 90, 2683
5.
MushkaloL.K., Zh. Obshch. Khim., 1958, 28, 507
6.
Hideg-HankovszkyO., and HidegK., Acta Chim.(Budapest), 1971, 68, 403.
7.
(a) StephensW.D., FieldL., J. Org. Chem., 1959, 24, 1576
