Synthesis Of New Serial Dibrominated Heterocycle-fused Troponoids

The chemistry of tropoind derivatives is derived from the chemistry of natural products. Its unique biological reactivity has attracted many organic chemists' attention, become the base of tropoind chemistry and been acted as the power of the development of non-benzene aromatic hydrocarbon.Tropoind compounds are a back-bone of many natural products and pharmacologically significant compounds displaying a broad range of biological activities. The tropoind skeleton is often used for the design of many synthetic compounds with diverse pharmacological properties. Many functionalized tropoind compounds are widely used as antibacterial, anti-inflammatory and antihypertensive agents. In order to develop new tropoind drugs and rich the theory of non-benzene aromatic hydrocarbon, 3-acetyltropolone as starting material was brominatedin by bromine in methanol to get compound 5,7-dibromo-3-acetyl-tropoind(l), from which the title compounds can be afforded.5,7-Dibromo-3-acetyl-tropoind(l) and substituent aromatic aldehydes had the aldol reaction under alkaline conditions. The reactions proceeded at room temperature and stirred for 36h and then acidulated and recrystallized from glacial acetic acid to afford the substituent cinnamoyl tropoinds (2)-(16).The resulting cinnamoyl tropoinds (2)-(16) had the oxidation and cyclization reactions in the I2/DMSO/H2SO4 system at refluxing temperature for l0h to give the 2-aromatic substituted-4,9-dihydrocyclohepo[b]pyran-4,9-diones(17)-(31).5,7-Dibromo-3-acetyl-tropoind(l) reacted with substituent benzaldehydes in the presence of ethanol at reflux temperature to afford troponyl-pyrazols compounds(32)-(37).All of these resulting compounds are very pure and have short melting range. Some of them were confirmed by IR, lH NMR and MS and some were confirmed by IR.