Phase Synthesis Of Quinoline Polymer-supported Reagents Participation And Selenium Compounds Dihydronaphthalene Solid

The formation of carbon-carbon bonds is one of the main parts of the organic synthesis. The development of various of new efficient methods to form carbon-carbon bond and their applications has become a focus of study for organic chemists. As a novel and creative technique, the combinatorial chemistry gives a vast potential for the synthesis and screening of the lead compounds.Quinolines are one of the major classes of heterocycles and the quinoline ring system is found in many natural products. Substituted quinolines are widely used in medicinal chemistry particularly as antituberculosis, antimalaria, anticancer and antivial agents. Herein, a method for synthesizing substituted-quinolines using TMSOTf-catalyzed polystyrene-supported succinimidyl selenide-induced intramolecular seleno-arylation of tethered alkenes as a key step has been developed. The catalytic process provides an efficient method for the stereoselective and regioselective synthesis of tetrahydroquinoline possessing a seleno-functionality, followed by deprotection of tosyl group and syn-elimination of selenoxides to provide quinolines in good yields and purities. This method offered several advantages like mild reaction, easy to operate, convenient to separate, good yields of products and high purity.Naphthalenes are a class of important intermediates in organic synthesis and have a variety of pharmacological activities such as antifungal, antineoplastic and antiparasitic activity. Naphthalenes has been wildly used in the pharmaceutical industry. Herein, we have developed a new method for the solid-phase synthesis of dihydronaphthalene compounds using1%cross-linking of polystyrene-supported succinimidyl selenide as the selenium source. In the presence of10mol%TMSOTf,4-cyano-4-phenyl-l-butene reacted polystyrene-supported succinimidyl selenide at-78℃to-20℃to afford polystyrene-supported seleno tetradydronaphthalene. This catalytic process provides an efficient method for the regioselective synthesis of polymer-suppoted tetrahydronaphthalenes possessing a seleno-functionality, followed by syn-elimination of selenoxides to provide1-cyano-4-phenyl-dihydronaphthalenes in good yields. Advantages of this method are ease in operations, odorlessness, and ease in preparation of the substrates. In addition,1-alkyl-l-cyano-4-phenyl-dihydronaphthalenes were synthesized by the alkylation of polymer-suppoted tetrahydronaphthalene in the presence of sodium alcoholate and subsequent syn-elimination of selenoxides.