Facile preparation of 4-substituted quinazolines and related heterocycles

摘要

A straightforward single step method for the preparation and/or production of substituted quinazolines is disclosed, wherein said quinazolines preferably contain one substituent at position 4, and may contain other functional groups at various positions, such as 5, 6, 7, and/or 8 of quinazolines. In addition, the extension of this new method leads to the formation of different type of heterocyclic aromatic compounds, that include but are not limited to perimidines, anthrapyrimidin-7-ones (also known as anthrapyrimidinones), anthra[1,9:5,10]dipyrimidines (also known as quinazoline[5,4-ef]perimidines) and benzo[e]-pyrimido[4,5,6-gh]pyrimidines.

主权项

1. A method for forming a quinazoline derivative, comprising the steps of:
providing thiourea as a reagent; providing a starting material comprising a 2-aminoarylcarbonyl compound, wherein the 2-aminoarylcarbonyl compound has a structure of: wherein R1 is independently selected from H, F, Cl, Br, I, NO2, CF3, alkyl, and aryl groups, wherein R1 is present at any one, any two, any three, or all four available ring positions, wherein R2 is an aryl or alkyl group of less than two α-hydrogen atoms, and wherein R3 is selected from H, alkyl, C(O)alkyl, C(O)aryl, and C(O)NMe2; mixing said thiourea and said starting material to form a mixture; and reacting said mixture in a solvent of high boiling point, said solvent selected from the group consisting of water, DMF, DMSO, ethylene glycol, 2-methoxyethanol, diethylene glycol monoethyl ether, p-dichlorobenzene, and combinations thereof at a temperature ranging from 75° C. to 185° C. to yield said quinazoline derivative, wherein said quinazoline derivative has a structure selected from: wherein R1 and R18 are independently selected from H, F, Cl, Br, I, NO2, CF3, alkyl, and aryl groups, wherein R1 is present at any one, any two, any three, or all four available ring positions and R18 is present at any one, any two, any three, any four, or all five available ring positions, and wherein R2 is an alkyl group of less than two α-hydrogen atoms.