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Interaction of 1,3λ 4 δ 2 ,2,4-benzodithiadiazines with neutral and charged S-electrophiles: SCl 2 , C 6 F 5 SCl, and NS 2 +
Chemistry of Heterocyclic Compounds ( IF 1.4 ) Pub Date : 2020-08-21 , DOI: 10.1007/s10593-020-02760-y
Alexander Yu. Makarov , Irina Yu. Bagryanskaya , Vladimir V. Zhivonitko

Reactions of 1,3λ4δ2,2,4-benzothiadiazines with SCl2, C6F5SCl, and [NS2][SbF6] leading to 1,2,3-benzodithiazolium salts (Herz salts) were investigated. The relative rate of reaction with SCl2 significantly depends on the nature of the substituent and its position in the carbocycle. Halogen substituents Cl, Br, and I slow down the reaction, especially if located closely to the heterocycle (positions 5 and 8). In the case of C6F5SCl and R = H, chlorination of the carbocycle and opening of the heterocycle also takes place with the formation of 7-chloro-1,3λ4δ2,2,4-benzothiadiazine and C6F5–S–N=S=N–Ar (Ar = 2-Cl-6-F5C6SC6H3), respectively. In the reaction with NS2+, along with contraction of the heterocycle, also its expansion occurs with the formation of 1,2,4λ4δ2,3,5-benzotrithiadiazepine.


中文翻译:

1,3λ4δ2,2,4-苯并二噻二嗪与中性和带电S-亲电试剂的相互作用:SCl 2,C 6 F 5 SCl和NS 2 +

的1,3λ反应4 δ 2,2,4- benzothiadiazines SCL为2,C 6 ˚F 5 SCL,和[NS 2 ] [的SbF 6 ]导致1,2,3- benzodithiazolium盐(赫茨盐)进行了调查。与SCl 2的相对反应速率显着取决于取代基的性质及其在碳环中的位置。卤素取代基Cl,Br和I减慢了反应的速度,尤其是如果其紧邻杂环(位置5和8)。在C的情况下,6 ˚F 5 SCL和R = H,杂环的碳环和开口的氯化也发生与7-氯1,3λ形成4δ 2,2,4-苯并噻二嗪和C 6 ˚F 5 -S-N = S = N-Ar(气体的Ar = 2-CL-6-F 5 C ^ 6 SC 6 ħ 3)表示。与NS反应2 +,具有杂环的收缩沿,也其扩张与1,2,4λ的形成发生4 δ 2,3,5- benzotrithiadiazepine。
更新日期:2020-08-21
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