Abstract: 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, Ⅰc) was synthesized from caprolactam and acrylonitrile, and five new photo base generators (PBGs) were prepared from DBU with five substituted benzyl chlorides by the two steps method. All the products and intermediates were characterized by LC-MS, 1H NMR and HPLC. The results indicated that the yield of compound Ⅰa was 98.1% and its purity was up to 97.8% when caprolactam and acrylonitrile reacted at 70 ℃ for 24 h in the presence of KOH. Ia was reduced by nickel to prepare Ⅰb, the yield was 91.1% and the purity was up to 98.0%. Moreover, in the presence of p-toluenesulfonic acid caprolactam and acrylonitrile reacted for 7.5 h, the cyclization yield of compound (Ⅰc) was up to 97.3% and the purity was more than 95.0%. Ⅰc reacted with benzyl chloride to synthesize the chloride salt of Ⅱa at 90 ℃, and then reduced to Ⅱa with hydrogenated lithium aluminum (0.7eq) at the yield of 76.7% and the purity reached 93.2%. Another four kinds of new PBGs were obtained by this method with the yield more than 70.0%, which indicated that the two steps method was appropriate for the synthesis of new PBGs. This improved the application of DBU and had great value for further study of PBGs.

Key words: DBU, new photo base generator, synthesis process, application value

摘要： 以ε-己内酰胺和丙烯腈为原料，反应合成1, 8-二氮杂双环（5, 4, 0）-7-十一烯（DBU，Ⅰc），再以DBU分别和5种取代基氯苄经两步法合成5种新型取代苄基脒类光产碱剂，产品及中间产物经1HNMR、LC-MS和HPLC进行结构表征和含量测试。结果表明：以ε-己内酰胺和丙烯腈为原料，氢氧化钾为催化剂，在70 ℃下，反应24 h，产物Ⅰa收率98.1%，纯度97.8%；以镍加氢方法，在85～90℃下，反应5 h将Ⅰa还原得产物Ⅰb，收率91.1%，纯度98.0%；以对甲基苯磺酸为催化剂，Ⅰb经环合反应7.5 h得Ⅰc，收率97.3%，纯度大于95.0%；以DBU（Ⅰc）和氯化苄为原料，在90 ℃下反应成盐，再以0.7当量的氢化铝锂还原得Ⅱa，收率达到76.7%，纯度93.2%；以先成盐再还原方法可成功合成4种取代苄基DBU类光产碱剂，收率均达到70%以上，说明此方法普遍适用此类光产碱剂的合成，提高了DBU的应用价值，也为进一步的研究奠定理论基础。

关键词: 1, 8-二氮杂双环（5, 4, 0）-7-十一烯, 新型光产碱剂, 合成工艺, 应用价值