Condensed thiophenes from sulfur bridging. II. Catalyzed reaction of azabiaryls with hydrogen sulfide

Sulfur bridging inlo the phenylpyridines, 2- and 3-phenylquinolines, and the symmetric bi-pyridines was effected by means of hydrogen sulfide and an alumina catalyst at 630° to give [1]benzothienopyridines, [1]benzothienoquinolines, and thienodipyridines, respectively. Structures of products were assigned on the bases of spectral and chromatographic studies, as well as of separate syntheses. Relative yields of the various products are rationalized in terms of a model for interaction between a chemisorbed sulfur atom and the substrate molecule.

[1]  D. R. Olson,et al.  Condensed thiophenes from sulfur bridging. I. Phenanthro[4,5-bcd]thiophene , 1970 .

[2]  C. E. Klopfenstein,et al.  2-Acetylbenzo[f]quinoline by direct synthesis of a β-acylpyridine structure , 1970 .

[3]  L. Klemm,et al.  Chemistry of thienopyridines. X. Syntheses of thieno[3,4‐b] — and thieno[3,4‐c] pyridines , 1970 .

[4]  L. Klemm,et al.  Chemistry of thienopyridines. VII. Mechanistic studies on the synthesis of thieno[2,3‐c] pyridine by thermolytic cyclization , 1969 .

[5]  C. E. Klopfenstein,et al.  Chemistry of thienopyridines. III. Syntheses of the thieno[2,3-b]- and thieno[3,2-b]pyridine systems. Direct substitution into the former system , 1969 .

[6]  C. E. Klopfenstein,et al.  Thin-layer chromatography of monoalkyl- and polymethylarenes on alumina , 1967 .

[7]  L. Snyder.  The adsorption of azaaromatics on alumina: a comment on the paper of Klemm, Kloppenstein and Kelley. , 1967, Journal of chromatography.

[8]  R. H. Martin,et al.  Applications de la spectrographie de resonance magnetique nucleaire (R.M.N.) dans le domaine des derives polycycliques a caractere aromatique—VI : Dérivé aza-aromatiques polycondensés☆☆☆ , 1964 .

[9]  S. Airee,et al.  GAS-SOLID ADSORPTION CHROMATOGRAPHY OF SOME AROMATIC HYDROCARBONS AND NITROGEN HETEROCYCLES ON ALUMINA. , 1964, Journal of chromatography.

[10]  L. Snyder.  ADSORPTION FROM SOLUTION. III. DERIVATIVES OF PYRIDINE, ANILINE, AND PYRROLE ON ALUMINA , 1963 .

[11]  L. Snyder.  ADSORPTION FROM SOLUTION. I. FUSED AROMATIC HYDROCARBONS ON ALUMINA , 1963 .

[12]  L. Snyder.  Linear elution adsorption chromatography. IV. Group localization in the adsorbate. Extension of the role of solute structure in separations over alumina. , 1962, Journal of chromatography.

[13]  L. Klemm,et al.  Chromatographic adsorption of azobenzenes and aromatic nitrogen heterocycles on alumina studies with alumina-impregnated glass paper , 1961 .

[14]  L. Snyder.  Linear elution adsorption chromatography: II. Compound Separability with alumina as adsorbent , 1961 .

[15]  C. H. Jarboe,et al.  Pyridine Analogs of p-Terphenyl and p-Quaterphenyl , 1960 .

[16]  B. Ho,et al.  Chemical Structure and Chromatographic Adsorbability of Aromatic Hydrocarbons on Alumina1,2,3 , 1959 .

[17]  C. H. Jarboe,et al.  Substituted 4,7-Phenanthrolines and Benzo[f]quinolines as Scintillation Solutes , 1958 .

[18]  E. Eliel,et al.  Chichibabin Reactions with Phenylacetaldehyde. II1 , 1956 .

[19]  I. Chibata,et al.  Application of ion exchangers in organic reactions. V. Application to the Friedländer quinoline synthesis. , 1955, Pharmaceutical bulletin.

[20]  G. Smith.  Ferroine, Cuproine, and Terroine Reacting Organic Analytical Reagents , 1954 .

[21]  W. Herz,et al.  Sulfur Analogs of Isoquinolines and β-Carbolines. III. The Pomeranz—Fritsch Reaction , 1953 .

[22]  H. Lochte,et al.  The Emmert Reaction in the Synthesis of Alkyl- and Cycloalkylpyridines1 , 1953 .

[23]  C. S. Hamilton,et al.  Thianaphtheno [3,2-c]pyridine and Certain Derivatives , 1953 .

[24]  C. R. Smith.  SKRAUP'S REACTION APPLIED TO THE PHENYLENEDIAMINES. PREPARATION OF THE PHENANTHROLINES AND RELATED DIPYRIDYLS , 1930 .

[25]  K. Fries,et al.  Zur Kenntnis des Thionaphtens , 1929 .

[26]  E. Noelting,et al.  Über die Kondensationsprodukte der Isatinsäure mit Oxy-thionaphthen, Indandion und Indanon , 1911 .

[27]  E. Nölting,et al.  Über Chindolin und Thiochindolin , 1910 .