Bakhite E A, Radwan S M
Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt.
Pharmazie. 1999 Jul;54(7):491-8.
The reaction of 7-chlorothieno[2,3-f]-1,3-benzodioxole-6-carbonyl chloride (2) with some aromatic or heterocyclic amines gave the corresponding 6-(aryl or heterocyclyl) carbamoyl-7-chlorothieno [2,3-f]-1,3-benzodioxoles (3a-c, 4a, b and 5). Compound 2 was also reacted with potassium thiocyanate, ethanol or sodium azide to afford the isothiocyanto compound 6, the ester 7 and the acid azide 9, respectively. Hydrazinolysis of 7 gave the carbohydrazide 8. The compounds 6, 8 and 9 were used as precursors in the synthesis of the target heterocycles, 7-chlorothieno[2,3-f]-1,3-benzodioxoles substituted with a variety of moieties at position-6 (10-15, 17, 19-26, 28-31). Also, 2-methyl-1,3-dixolo[5,6][1]benzothieno[2,3-c]quinolin- 6(5 H)-one (33) was prepared. The antibacterial and antifungal activities of some selected compounds were also reported.
7-氯噻吩并[2,3-f]-1,3-苯并二恶唑-6-甲酰氯（2）与一些芳香胺或杂环胺反应，生成相应的6-（芳基或杂环基）氨基甲酰基-7-氯噻吩并[2,3-f]-1,3-苯并二恶唑（3a - c、4a、b和5）。化合物2还分别与硫氰酸钾、乙醇或叠氮化钠反应，得到异硫氰酸酯化合物6、酯7和酰基叠氮化物9。7经肼解得到碳酰肼8。化合物6、8和9用作合成目标杂环化合物的前体，这些杂环化合物是在6位被各种基团取代的7-氯噻吩并[2,3-f]-1,3-苯并二恶唑（10 - 15、17、19 - 26、28 - 31）。此外，还制备了2-甲基-1,3-二恶唑并[5,6][1]苯并噻吩并[2,3-c]喹啉-6(5H)-酮（33）。还报道了一些选定化合物的抗菌和抗真菌活性。
