Isopropyl N-arylmalonamates. Synthesis, structure, conformation and reactions with carbon disulfide
Acylation of aromatic amines 1 with diisopropyl malonate (2) leads to a mixture of isopropyl N-arylmalonamates 3 and malonanilides 4. The reaction of 3 with carbon disulfide in the presence of sodium hydride gives disodium salts 5. Treatment of 5 with an alkylating agent yields the open-chain or cyclic ketene dithioacetals 6, 7 or 8. The molecular structure, hydrogen bonding and preferential conformation of the isopropyl N-arylmalonamates 3, 6 and 7 were investigated using correlation analyses of IR, 13C NMR and AMI semiempirical data.
Synthesis of Benzo-halogenated 4-Hydroxy-2(1H)-quinolones
Malondianilides 3 derived from dichloro substituted anilines 2 undergo cyclization to afford 4-hydroxy-2(1H)-quinolones 4 in very good yields using methane sulfonic acid-phosphorus pentoxide as catalyst. 3,4-Dichloro anilines 5 can be shown to yield two i
Kappe, Thomas,Karem, Abdel S.,Stadlbauer, Wolfgang
p. 857 - 862
(2007/10/02)
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