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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 84, 1993 - Issue 1-4
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Communication

SYNTHESES OF S,N-HETEROCYCLES FROM N-THIOACYLLACTAMIMINES

J. Bohrisch Institut für Organische und Bioorganische Chemie, Humboldt-Universität, Hessische Str. 1-2, 10115, Berlin, Germany
,
M. Pätzel Institut für Organische und Bioorganische Chemie, Humboldt-Universität, Hessische Str. 1-2, 10115, Berlin, Germany
,
L. Grubert Institut für Organische und Bioorganische Chemie, Humboldt-Universität, Hessische Str. 1-2, 10115, Berlin, Germany
&
J. Liebscher Institut für Organische und Bioorganische Chemie, Humboldt-Universität, Hessische Str. 1-2, 10115, Berlin, Germany
Pages 253-256 | Received 30 Aug 1993, Published online: 23 Sep 2006
 
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Abstract

Nitrile imines undergo cycloadditions to the thiocarbonyl group of N-thioacyllactamimines 1 giving 1,3,4-thiadiazolines 2. Depending on the substituents oxidation of N-thioacyllactamimines 1 leads to different products, such as condensed 5-amino-1,2,4-thiadiazolium bromides 5, 3,5-diaryl-1,2,4-dithiazolium salts 6, 3,5-diaryl-1,2,4-thiadiazoles 7 or 2-benzothiazolyliminopyrrolidine 8.

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Related Research Data

Synthese von cyclischen N-Thioacyl-amidinen aus Aminothiocarbonylverbindungen und aktivierten Lactamen
Source: Wiley
Ring Transformations of Semicyclic 1,3-Dicarbonyl Heteroanalogs; IV1. Synthesis of 3-(ω-Aminoalkyl)-1,2,4-thiadiazoles by Ring Transformation Reaction of Semicyclic Thioacylamidines with 3,3-Pentamethyleneoxaziridine
Source: Georg Thieme Verlag KG
Oxydationsprodukte von Thiocarbonsäureamiden, III. Oxydationsprodukte primärer Thioamide
Source: Wiley
Reaction of heterocyclic ketene aminals with aryl isothiocyanates and synthesis of sulfur containing heterocycles therefrom
Source: Wiley
Synthesis of Heterocycles by reaction of semicyclic 2‐Aza‐3‐methylthio‐propeniminium salts with 1,4‐ and 1,5‐binucleophiles
Source: Wiley
The mass spectrometry of 1,3,4-thiadiazolines
Source: Wiley
Ring Transformations of Semicyclic 1,3-Dicarbonyl Heteroanalogs; I. Synthesis of Semicyclic N-Acyl- and N-(Aminocarbonyl)amidine Derivatives and Their Ring Transformation to 5-(ω-Aminoalkyl)-1,2,4-triazoles
Source: Georg Thieme Verlag KG
Oxidation von Thioamiden; eine einfache Synthese von neuartigen 3,5‐Diaryl‐1,2,4‐dithiazoliumsalzen
Source: Wiley
Synthesis of 1,1-diamino-2-thioacylethylenes: A novel C-thioacylation by the Willgerodt-Kindler reaction
Source: Elsevier BV

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