Studies on nucleoside analogs. XIX. Reaction of D-gluconyl isothiocyanate with diamines or enamines.
- 1 January 1981
- journal article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 29 (7) , 1832-1837
- https://doi.org/10.1248/cpb.29.1832
Abstract
The reaction of phenylacetyl isothiocyanate (1a) with diamines afforded 1-substituted 3-phenylacetyl thiourea (3a-d) in good yields. Attempted ring closure of these products under thermal or basic conditions was unsuccessful. However, treatment of 3a with Ac2O-H3PO4 at room temperature gave the cyclized product (5a). Similar reaction of D-gluconyl isothiocyanate (1b) with o-phenylenediamine (2a) or diaminopyrimidines (2b, c, e, f) gave the D-gluco-pentyl benzotriazepine-2-thione (7a) or D-gluco-pentyl pyrimidotriazepine-2-thiones (7b, c, e, f), respectively, in fair yields. Treatment of 1b with ethyl 3-aminocrotonate or 6-amino-1, 3-dimethyluracil afforded D-gluco-pentyl thiopyrimidine (8b) or D-gluco-pentyl pyrimido [4, 5-d] pyrimidine (9b), respectively.Keywords
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