CN112521384B - 溶剂热一锅法合成苯并噻嗪并环戊二烯衍生物 - Google Patents
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Abstract
本发明公开了结构通式(I)所示的化合物,其利用简单易得的苯并[d]噻唑‑2‑基甲醇衍生物在FeCl3·6H2O催化下,在醇类有机溶剂中,溶剂热条件下“一锅法”高产率得到产物,实现了苯并噻嗪并环戊二烯的高效制备,减少了中间产物分离提纯的步骤,进而减少了有机溶剂的使用,缩短合成周期,有较高的应用价值。
Description
技术领域
本发明涉及一种1,2,3-三(苯并[d]噻唑-2-基)-2,9-二氢苯并[b]环戊[e] [1,4]噻嗪及其衍生物的合成方法,属于有机合成技术领域。
背景技术
噻嗪是一类常见的六元环状有机化合物,由四个碳原子、一个氮原子以及一个硫原子组成。噻嗪应用广泛,通常被用作为染料、安定药以及杀虫剂等。然而,已报道的合成噻嗪环的方法需要复杂且昂贵的原料以及对水和空气敏感的格氏试剂,而且反应路线长,有的高达十步以上。目前,含噻嗪环有机化合物的高效合成依然是具有挑战性的课题。
发明内容
本发明的目的是提供一类苯并噻嗪并环戊二烯衍生物;
本发明的另一个目的是提供上述苯并噻嗪并环戊二烯衍生物的制备方法。
本发明实现过程如下:
结构通式(I)所示的化合物,
R选自氢,卤素基,C1-C5的烷基,C1-C5的烷氧基,苯基,氰基,N,N-二甲基,三氟甲基。
上述化合物的制备方法,
将化合物A溶于醇类有机溶剂中,加入催化量的六水合三氯化铁,在80~120 ℃密闭条件下充分反应得到化合物(I)。
所述醇类有机溶剂选自甲醇、乙醇或丙醇。
当R为氢时,得到的化合物的晶体学参数为:三斜晶系,P-1空间群,晶胞参数为a =8.7807(2) Å,b = 12.5902(3) Å,c = 13.7137(3) Å,α = 103.344(2) o,β = 106.821(2)o,γ = 104.749(2) o。
本发明利用简单易得的苯并[d]噻唑-2-基甲醇衍生物在FeCl3·6H2O催化下,在醇类有机溶剂中,在溶剂热条件下“一锅法”高产率得到产物,实现了苯并噻嗪并环戊二烯的高效制备,减少了中间产物分离提纯的步骤,进而减少了有机溶剂的使用,缩短合成周期,有较高的应用价值。
附图说明
图1为实施例1化合物L的结构图;
图2为实施例1化合物L的核磁氢谱;
图3为实施例1化合物L的电喷雾离子化高分辨质谱图;
图4为实施例1化合物L的热重分析图;
图5为实施例1化合物L的红外图;
图6为实施例1化合物L的紫外光谱吸收图;
图7为实施例1化合物L的荧光光谱图。
具体实施方式
为了更清楚的理解发明,以下通过发明人给出的依本发明技术方案所完成的具体实施例对本发明进一步的详细描述。
实施例1 L(R= H)的合成及结构分析
将1.0 mmol的苯并[d]噻唑-2-基甲醇(165.0 mg)加入到容积为15.0 mL的聚四氟乙烯的反应釜中,加入9.0 mL的乙醇溶解后,再加入1.0 mmol的六水合三氯化铁(268.0mg),搅拌5分钟,密封,放入120 ℃的烘箱中反应48 h,然后将釜取出,保持10℃ / h缓慢冷却,开釜得到紫红色晶体和红褐色母液。得到的化合物L属于三斜晶系,P-1空间群,晶胞参数为a = 8.7807(2) Å,b = 12.5902(3) Å,c = 13.7137(3) Å,α = 103.344(2) o,β =106.821(2) o,γ = 104.749(2) o。
1H NMR (400 MHz, CD2Cl2) δ 11.86 (s, 1H), 8.24-8.16 (m, 2H), 8.09 (d,J = 7.6 Hz, 1H), 7.84 (d, J = 8.0 Hz, 2H), 7.77 (d, J = 8.0 Hz, 1H), 7.72 (d,J = 8.0 Hz, 1H), 7.54-7.48 (m, 4H), 7.39-7.35 (m, 5H), 7.31-7.28 (m, 1H),7.16 – 7.12 (m, 1H), 6.04 (s, 1H)。
图1为L的单晶结构图,结果表明L是由苯并噻嗪并环戊二烯三个杂环构成,其结构中包含由C-C单键连接的联苯并噻唑单元。化合物L的空间群是P-1,该结构中C1-C5,N6,C7-C12,S13这13个原子构成的三个环距离最小二乘面的距离最大的是C3距离是0.069 Å,说明这13个原子共平面性很好,并且符合4n+2的规则。C1-C2键长1.360 Å,C4-C5键长1.369 Å属于碳碳双键。
图2为L的核磁氢谱表明与L的单晶结构一致。
图3为L的电喷雾离子化高分辨质谱图,m/z在585.0336处的峰为分子离子峰[L-H]+,验证了L分子式为C32H18N4S4,同时表明其在质谱条件下的骨架稳定性。
图4为化合物L2的热重分析图,结果表明氮气气氛下L在360 ℃开始分解,且到800℃时质量仍有约50%剩余,表明有较好的热稳定性,同时表明L中无客体分子。
上述化合物实验测试条件如下:
1.核磁谱图
室温下,在Bruker 400 MHz上进行L的核磁共振谱图测试,取10.0 mg的L溶于0.5mL的CD2Cl2中进行测试,得到的谱图结果与单晶结构相吻合。
2.高分辨质谱图
室温下,取1颗单晶溶于色谱级乙腈中,在Thermo Exactive Plus ESI-MS 上进行阳离子模式下的数据采集。
3.热重图
室温下称取7 mg的L,在Netzsch TG209F3上进行L热稳定测试,其中加热区间为30-800 oC,升温速率为10 oC/min,氮气流速为15 mL/min。
4.红外光谱
室温下,在Bruker FTIR spectrophotometer上进行L的红外测试,取0.1 mg的L制成KBr压片,测试范围为4000-400 cm-1,测试结果如图5所示。
5.紫外-可见吸收光谱
室温下,在Agilent Cary 6000UV-Vis-NIR spectrophotometer上对L的二氯甲烷溶液(10-5 mol·L-1)进行测试。如图6所示,L的二氯甲烷溶液在365 nm和450 nm有最大吸收峰,可以归属为π-π*跃迁。
6.荧光发射
室温下在爱丁堡FLS-980荧光仪上对L的二氯甲烷溶液(10-5 mol·L-1)进行测试。如图7所示,在波长为264 nm光激发下,在可见-近红外(390-600 nm)具有荧光发射, 664nm为最大发射波长。
实施例2
参照实例1制备方法,使用不同的原料,可制备得到相应的苯并噻嗪并环戊二烯衍生物,其结果如表1所示
Claims (6)
2.根据权利要求1所述的化合物,其特征在于:R选自氢,氟,氯,甲基,乙基,苯基,甲氧基,氰基,N,N-二甲基,三氟甲基。
3.根据权利要求2所述的化合物,其特征在于:R选自氢。
4.根据权利要求3所述的化合物,其特征在于所述化合物的晶体学参数为:三斜晶系,P-1空间群,晶胞参数为a = 8.7807(2) Å,b = 12.5902(3) Å,c = 13.7137(3) Å,α =103.344(2) o,β = 106.821(2) o,γ = 104.749(2) o。
6.根据权利要求5所述化合物的制备方法,其特征在于:所述醇类有机溶剂选自甲醇、乙醇或丙醇。
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