157868-96-7Relevant academic research and scientific papers
Richter cyclization and co-cyclization reactions of triazene-masked diazonium ions
Goeminne, Annelies,Scammells, Peter J.,Devine, Shane M.,Flynn, Bernard L.
, p. 6882 - 6885 (2011/03/18)
The conventional Richter cyclization involves diazotization of 2-alkynylanilines with HX (aq) (X = Br or Cl) and NaNO2, followed by spontaneous ring closure to give a mixture of 4-halocinnoline and 4-cinnolinone products. The different products
Solid-phase synthesis of substituted cinnolines by a Richter type cleavage protocol
Braese, Stefan,Dahmen, Stefan,Heuts, Jean
, p. 6201 - 6203 (2007/10/03)
Starting from triazene bound ortho-halo arenes on a solid support, palladium-catalyzed alkynylations and subsequent cleavage reactions under acidic conditions give rise to ortho-alkynylaryldiazonium salts, which in turn undergo cyclization to afford substituted 4-halo- and 4- hydroxycinnolines in moderate to good yields. The method is applicable to automated synthesis.
Cinnolines and Pyrazolopyridazines. - Novel Synthetic and Mechanistic Aspects of the Richter Reaction
Vasilevsky, Sergei F.,Tretyakov, Eugene V.
, p. 775 - 780 (2007/10/02)
The thermal cyclization of 2-alkynylbenzenediazonium salts 2 known as the Richter reaction and leading, as described in the literature, only to 4-hydroxycinnolines 6 has been studied.A new probable route to these compounds involving intermediate formation
A convenient synthesis of 4-chloro- and 4-bromocinnolines from o- aminophenylacetylenes
Vasilevsky,Tretyakov,Verkruijsse
, p. 1733 - 1736 (2007/10/02)
4-Chlorocinnolines and 4-bromocinnolines have been obtained in fair to good yields by diazotation of o-aminophenylacetylenes with sodium nitrite and concentrated hydrochloric acid or hydrobromic acid at temperatures between 25 and 30°C.
