THIAZOLOISOQUINOLINES: I. THE SYNTHESIS OF THIAZOLO[4,5-c]ISOOUINOLINE

1966 ◽  
Vol 44 (21) ◽  
pp. 2465-2472 ◽  
Author(s):  
Catherine E. Hall ◽  
Alfred Taurins
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Hydrochloric Acid ◽  
Potassium Thiocyanate ◽  
Heterocyclic Ring ◽  
Ring System ◽  
Hydrogen Iodide ◽  
Red Phosphorus ◽  
Nucleophilic Displacement ◽  
Derivatives Of

Thiazolo[4,5-c]isoquinoline (I), a new heterocyclic ring system, has been synthesized from 3-aminoisoquinoline (II) in four steps by reaction with potassium thiocyanate and bromine to give 3-amino-4-thiocyanoisoquinoline (VII), cyclization with hydrochloric acid to yield 2-aminothiazolo[4,5-c]isoquinoline (VIII), Sandmeyer reaction to give 2-chlorothiazolo-[4,5-c]isoquinoline (IX), and finally reduction with hydrogen iodide and red phosphorus to yield I. The attempted preparation of I via 3-amino-4-bromoisoquinoline was unsuccessful. Various 2-substituted derivatives of I were prepared by nucleophilic displacement of the chlorine atom in 2-chIorothiazolo[4,5-c]isoquinoline. The nuclear magnetic resonance and ultraviolet spectra of I and some of its derivatives were studied.

Nuclear magnetic resonance characterization of the ring conformations of monosubstituted derivatives of 1,3-dioxa-5,6-benzocycloheptene

1983 ◽  
Vol 61 (1) ◽  
pp. 109-115 ◽  
Author(s):  
R. St-Amour ◽  
M. St-Jacques
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Substituent Effects ◽  
Steric Effects ◽  
Slow Exchange ◽  
Conformational Properties ◽  
Derivatives Of ◽  
Ring Conformations ◽  
Twist Boat

The conformational properties of 2-alkyl (Me, Et, i-Pr, and t-Bu) and 2-phenyl derivatives of 1,3-dioxa-5,6-benzocycloheptene (1) were studied by 13C dnmr. Analysis of slow exchange spectra at 100.6 MHz indicates that all derivatives except tert-butyl exist in an equilibrium of chair (major) and twist-boat (minor) conformations. Substituent effects on the position of the equilibrium are rationalized in terms of steric effects.

Analysis of the lipopolysaccharide of Pseudomonas maltophilia 555

1987 ◽  
Vol 65 (11) ◽  
pp. 968-977 ◽  
Author(s):  
Jose L. Di Fabio ◽  
Malcolm B. Perry ◽  
David R. Bundle
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Gel Electrophoresis ◽  
Polyacrylamide Gel Electrophoresis ◽  
Sodium Dodecyl ◽  
Brucella Species ◽  
Pseudomonas Maltophilia ◽  
Structure Formula ◽  
Derivatives Of ◽  
Acyl Derivatives

The phenol phase soluble lipopolysaccharide of Pseudomonas maltophilia strain 555, obtained from cells by the hot aqueous phenol method, was of the smooth type. Sodium dodecyl sulfate – polyacrylamide gel electrophoresis, hydrolysis, methylation, and 13C and 1H nuclear magnetic resonance analyses showed that this lipopolysaccharide has an O-chain polysaccharide composed of a repeating pentasaccharide unit, containing D-rhamnose (D-Rha, one part), 3-acetamido-3,6-dideoxy-D-galactose (D-Fuc3NAc, one part), and 4-acetamido-4,6-dideoxy-D-mannose (D-Rha4NAc, three parts) and having the structure[Formula: see text]The serological cross-reactions between P. maltophilia 555 and Brucella species can now be related to the occurrence of N-acyl derivatives of 4-amino-4,6-dideoxy-D-mannopyranosyl residues in the O-chains of their respective lipopolysaccharide components.

Sign in / Sign up

Export Citation Format

Share Document