Phosphorus, sulfur, and silicon and the related elements · 1995 · 11 citations · 8 references
PharmacyChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryHypnotic AgentsHypnotic PharmacotherapyHypnotic TherapyOrganic SynthesisBenzothiophene ChemistryHypnotic EffectsHypnotic MedicationsHypnotic PharmacologyPyrimidine ChemistrySedative-hypnotic Mechanisms
Abstract Ethyl-4,5,6,7-tetrahydro-2-isothiocyanato-1-benzothiophene-3-carboxylate (2), prepared from ethyl-4,5,6,7-tetrahydro-2-amino-1-benzothiophene-3-carboxylate (1) by the thiophosgene method, was converted with nucleophiles into benzothieno[2,3-d]pyrimidine derivatives (3–5) and (7) either directly or through thiourethane (6a). The tricyclic, benzothienopyrimidine systems (8) and (9) were obtained either from the isothiocyanate (2) or the thiourethane (6a), while the tetracyclic systems, triazolothienopyrimidines (10,11); tetrazolothienopyrimidines (12,13) and tetrazepino derivative (14), were obtained from 2,3,5,6,7,8-hexahydro-3-amino-2-hydrazino-1-benzothieno[2,3-d]pyrimidine-4(3H)-one (9). Preliminary pharmacological screening revealed that some of the new compounds exhibited hypnotic activity.
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Chemistry of heterocyclic compounds 751
B. A. Tertov, A. V. Koblik · Chemistry of Heterocyclic Compounds · 1969 · 172 citations
Frank Kienzle, A. Kaiser, Rudolf E. Minder · Helvetica Chimica Acta · 1983 · 49 citations
2,3-Dihydrothiazolo[2,3-b]quinazolin-5-one
John Howard, George M. Klein · The Journal of Organic Chemistry · 1962 · 41 citations