Über Thiazole, XII. Mitteilung: Synthesen von Thiazolyl‐(2)‐hydrazinen

Abstract

Es werden die Synthesen des Thiazolyl‐(2)‐hydrazins sowie des 4‐Methyl‐, 4‐Phenyl‐ und 4.5‐Diphenyl‐thiazolyl‐(2)‐hydrazins und deren Kondensationsprodukte mit Aldehyden und Ketonen beschrieben. Die Umsetzung von l Mol. Glucose mit 2 Moll. 4‐Phenyl‐thiazolyl‐(2)‐hydrazin in Gegenwart von l Mol Hydrazinhydrat führt zu dem gelben, gut kristallisierenden Glucose‐[4‐phenyl‐thiazolyl‐(2)]‐osazon.

Reaction of thiosemicarbazide with n-cyanoguanidine: synthesis of 3,5-diamino-1-thiocarbamoyl-and 3,5-diamino-1-thiazol-2-yl-1,2,4-triazoles

“…16 The phenyl substituent at the C(11) atom is virtually co planar with the plane of the thiazole ring (the C(12)-C(11)-C(13)-C(18) torsion angle is -5.1(2)°) in spite of the shortened intramolecular H (14)...N(6) and H (18)...C(12) contacts (2.54 and 2.74 Å, respectively; the corresponding sums of the van der Waals radii are 2.67 and 2.87 Å). One DMF molecule occupies a special position on a center of symmetry, which coincides with the position of the nitrogen atom.…”

Benzo- and naphthoimidazoxadiazolediene, naphthobisthiazole as well as naphthothiazine derivatives from 1-acylthiosemicarbazides

“…[25][26][27] . The 1 H-NMR spectral data of 1-acetylthiosemicarbazide (1a) 25 , 1-benzoylthiosemicarbazide (1b) 26 , and 1-(4-hydroxyphenyl)thiosemicarbazide (1c) 27 were in full accord with the published data.…”

Thiosemicarbazides in heterocyclization

“…4‐Phenyl thiosemicarbazide 1 reacts with α‐haloketones and yield 3‐amino‐2‐phenylimino‐4‐substituted‐Δ 4 ‐thiazolines 76 [50]. An extension of this approach was reported earlier [51].…”