Bromine‐induced cyclization of 1‐acyl‐3‐(3‐thienyl)‐2‐thioureas to 2‐acylaminothieno[3,2‐d]thiazoles
- 1 January 1978
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 15 (1) , 81-87
- https://doi.org/10.1002/jhet.5570150118
Abstract
Three different 1‐acyl‐3‐(3‐thienyl)‐2‐thioureas were cyclized to 2‐acylaminothieno[3,2‐d]thiazoles with bromine in acetic acid whereas the corresponding 2‐thienylthiourea derivatives were brominated under the same reaction conditions. The parent thieno[3,2‐d]thiazole was prepared by acid hydrolysis and deamination of 2‐benzoylaminothieno[3,2‐d]thiazole. This new heterocyclic compound was nitrated and brominated in the 5‐position.Keywords
This publication has 21 references indexed in Scilit:
- A facile synthesis of 2-aminothiazolo[5,4-b]- and 2-aminothiazolo[4,5-c] pyridinesJournal of Heterocyclic Chemistry, 1977
- 2‐Amino‐thieno [2,3‐d] thiazole und 3‐Amino‐thieno [2,3‐c]‐isothiazoleJournal für Praktische Chemie, 1973
- Ambident neighbouring groups, VI, the most powerful neutral neighbouring group - the N-arylthioureido group.Tetrahedron Letters, 1970
- Cyclizations of Thioureas with a Hydroxy Group at the β-Position of the N-Substituent. II. Oxidation with Thionyl Chloride to BenzothiazolesBulletin of the Chemical Society of Japan, 1970
- Dielectric relaxations and dipole moments of Di-t-butyl peroxide and of some dialkyl and diaryl disulphidesAustralian Journal of Chemistry, 1970
- Synthese und Substitutionsreaktionen von Acenaphtho‐(1,2‐b)‐thiophen und 1‐Methyl‐acenaphtho‐(1,2‐b)‐pyrrolJournal für Praktische Chemie, 1969
- Über die S-N‐Bindung, I. Bis‐guanyl‐disulfid‐Salze als Zwischenstufe der Bildung von 1.2.4‐Thiadiazolidinen und 2‐Amino‐benzthiazolenEuropean Journal of Inorganic Chemistry, 1967
- On a New Type of Rearrangement during Ring-closure.Acta Chemica Scandinavica, 1962
- AN ANTIMALARIAL ALKALOID FROM HYDRANGEA. XIX. THIOPHENE ISOSTERSThe Journal of Organic Chemistry, 1953
- III. Über 2‐ThiopheninEuropean Journal of Organic Chemistry, 1914