化学世界
化學世界
화학세계
CHEMICAL WORLD
2010年
3期
165-168
,共4页
2-乙氧基萘并吡喃并[2%3-d]嘧啶-4(3H)-酮%膦亚胺%aza-Wittig反应%合成
2-乙氧基萘併吡喃併[2%3-d]嘧啶-4(3H)-酮%膦亞胺%aza-Wittig反應%閤成
2-을양기내병필남병[2%3-d]밀정-4(3H)-동%련아알%aza-Wittig반응%합성
2-ethanoxy-naphtha[1′,2′ : 5,6]pyrano[2,3-d]pyrimidin-4 ( 3 H)-one%iminophosphorane%aza-Wittig reaction%synthesis
以2-萘酚、氰乙酸乙酯、4-氯苯甲醛为原料,以六氢吡啶有机碱为催化剂,无水乙醇为溶剂,通过Knoevenagl-Cope缩合得到2-氨基-3-乙氧羰基-4-(4-氯苯基)萘并吡喃(1),1再与三苯基膦、六氯乙烷及三乙胺反应得到膦亚胺中间体(2).2与4-氯苯基异氰酸酯在二氯甲烷的溶液中采用aza-Wittig反应,得到碳二亚胺(3).3与乙醇反应,经乙醇钠催化关环,合成了2-乙氧基萘并吡喃并[2,3-d]嘧啶-4(3H)-酮.实验考察了反应温度、反应时间、溶剂诸因素对膦亚胺收率的影响.结果表明:在反应温度5℃、反应时间6 h、乙腈为溶剂的优化条件下,产物收率为87.8%.产物结构经IR、~1H NMR、MS进行了表征.
以2-萘酚、氰乙痠乙酯、4-氯苯甲醛為原料,以六氫吡啶有機堿為催化劑,無水乙醇為溶劑,通過Knoevenagl-Cope縮閤得到2-氨基-3-乙氧羰基-4-(4-氯苯基)萘併吡喃(1),1再與三苯基膦、六氯乙烷及三乙胺反應得到膦亞胺中間體(2).2與4-氯苯基異氰痠酯在二氯甲烷的溶液中採用aza-Wittig反應,得到碳二亞胺(3).3與乙醇反應,經乙醇鈉催化關環,閤成瞭2-乙氧基萘併吡喃併[2,3-d]嘧啶-4(3H)-酮.實驗攷察瞭反應溫度、反應時間、溶劑諸因素對膦亞胺收率的影響.結果錶明:在反應溫度5℃、反應時間6 h、乙腈為溶劑的優化條件下,產物收率為87.8%.產物結構經IR、~1H NMR、MS進行瞭錶徵.
이2-내분、청을산을지、4-록분갑철위원료,이륙경필정유궤감위최화제,무수을순위용제,통과Knoevenagl-Cope축합득도2-안기-3-을양탄기-4-(4-록분기)내병필남(1),1재여삼분기련、륙록을완급삼을알반응득도련아알중간체(2).2여4-록분기이청산지재이록갑완적용액중채용aza-Wittig반응,득도탄이아알(3).3여을순반응,경을순납최화관배,합성료2-을양기내병필남병[2,3-d]밀정-4(3H)-동.실험고찰료반응온도、반응시간、용제제인소대련아알수솔적영향.결과표명:재반응온도5℃、반응시간6 h、을정위용제적우화조건하,산물수솔위87.8%.산물결구경IR、~1H NMR、MS진행료표정.
2-Aminonaphtha[1′, 2′: 5, 6]pyrano-3-carboxylate (1), obtained from Knoevenagl-Cope condensation reaction of 2-naphthol, ethyl cyanoacetate and 4-chlorobenzaldehyde using hexahydropyridine as catalyst and absolute ethyl alcohol as solvent, reacted with triphenylphosphine, hexachloroethane and triethylamine to give iminophosphorane (2). Further aza-Wittig reactions of 2 with phenyi isoeyanate using dichloromethane as solvent gave carbodiimide (3), which reacted with ethyl alcohol to give 2-ethanoxy-naphtha[1′, 2′: 5, 6]pyrano[2, 3-d]pyrimidin-4 (3H)-one in the presence of EtONa. The factors influencing the synthesis were investigated and the best reaction conditions were found. The optimum conditions were: reaction temperature of 5 ℃, reaction time of 6 h, and acetonitrile as solvent. The yield reached 87.8%. The product compounds were identified by using IR,~1 H NMR and MS spectroscopy.
