A furan ring expansion approach to the synthesis of novel pyridazino-psoralen derivatives |
| |
Authors: | José C González-Gómez Lourdes Santana Eugenio Uriarte |
| |
Institution: | Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain |
| |
Abstract: | A convenient preparation of the parent tetrahydrobenzodifuran 2 was developed from resorcinol. The oxidation of one or both furan rings of this key intermediate was accomplished with DDQ and the resulting benzodifuran was subsequently reacted with 3,6-dimethoxycarbonyl-1,2,4,5-tetrazine to afford the expected pyridazino-psoralen derivative in good yield. This simple method allowed the efficient preparation of a pyridazino-psoralen derivative with a formyl group at C-7, which was introduced by directed ortho-lithiation in the intermediate 2. An aminoalkyl side-chain was also introduced to the tetracyclic skeleton through the aldehyde functionality in a reductive amination process, which was accompanied by an unprecedented reduction of the pyridazine ring. |
| |
Keywords: | Psoralens Benzofurans Tetrazines Diels-Alder DNA intercalants |
本文献已被 ScienceDirect 等数据库收录! |
|