New heterocyclic derivatives of 1′‐ and 3′‐amino‐5′,6′,7′,8′‐tetrahydro‐2′‐acetonaphthones

Abstract

The preparation of 1′‐and 3′‐amino‐5′,6′,7′,8′‐tetrahydro‐2′‐acetonaphthones (IIIa and IIIb) is described, by reduction of the low temperature nitration products of 5′,6′,7′,8′‐tetrahydro‐2′‐acetonaphtone (I). The structures of the nitro isomers (IIa and IIb), and the reduction products, IIIa and IIIb, were elucidated spectroscopically. By known reactions, a series of new heterocyclic compounds prepared from the o‐aminoketones, IIIa and IIIb, resulted in two series of new heterocyclic compounds.

Synthesis of 4-substituted imino-4H-benzo[d][1,3] thiazin-2-amines via palladium-catalysed isocyanide insertion in 2-bromophenylthioureas

“…The classical methods involve the condensation of aromatic amine or thioureas bearing an ortho halomethyl, hydroxymethyl or cycloalkyl or oxirane with thioamides or thioureas in the presence of base or Bronsted acid. [5][6][7] But recently the approach involving a 6-exodig type addition/cyclization of 2-ethynylaniline with isothiocyanate or related compounds or 2-ethynylphenylisothiocyanates with amines oen promoted by silver catalyst, DMAP, silica gel or iodine has attracted considerable attention. 8 Simultaneously, another protocol involving tandem addition/ cyclization of 2-aminocinnamate with isothiocyanates promoted by Lanthanide salts or reaction of 3-(2-isothiocyanatophenyl)propenoic acid derivatives with secondary amines under heating for preparing 4H-benzo[d][1,3]thiazin-2-amines has also been expounded recently.…”