التفاصيل البيبلوغرافية
| العنوان: |
The preparation of dicyano-1,3,4-thiadiazole and tricyanothiazole via 1,2,3-dithiazole chemistry |
| المؤلفون: |
Christoforou, Irene C., Kalogirou, Andreas S., Koutentis, Panayiotis Andreas |
| المساهمون: |
Koutentis, Panayiotis Andreas [0000-0002-4652-7567], Christoforou, Irene C. [0000-0001-6624-3548], Kalogirou, Andreas S. [0000-0002-5476-5805] |
| المصدر: |
Tetrahedron |
| بيانات النشر: |
Elsevier BV, 2009. |
| سنة النشر: |
2009 |
| مصطلحات موضوعية: |
thiazole derivative, Reaction mechanism, 5 cyano 1,3,4 thiadiazole 2 carboxamide, Nitrile, acetonitrile derivative, polymer, Iodide, Hydrazine, phosphine derivative, 2,3 bis(4 chloro 5h 1,2,3 dithiazol 5 ylideneamino)maleonitrile, tricyanothiazole, Biochemistry, Medicinal chemistry, Chemical synthesis, isomerization, triphenylphosphine, chemistry.chemical_compound, benzyltriethylammonium iodide, Drug Discovery, Organic chemistry, Triphenylphosphine, Acetonitrile, (dithiazolylidene)acetonitrile, 2 (4 chloro 5h 1,2,3 dithiazol 5 ylideneamino) 2 (4 chloro 5h 1,2,3 dithiazol 5 ylidene)acetonitrile, chemistry.chemical_classification, 1,2 bis(4 chloro 5h 1,2,3 dithiazol 5 ylidene)hydrazine, 2,3 bis (4 chloro 5h 1,2,3 dithiazol 5 ylideneamino)fumaronitrile, irradiation, Chemistry, Organic Chemistry, article, unclassified drug, hydrazine derivative, isomer, priority journal, Yield (chemistry), sodium chloride, chemical structure, chromatography, thiadiazole derivative, iodide, dicyano 1,3,4 thiadiazole, pyrrole derivative, 1,2,3 dithiazole |
| الوصف: |
Treatment of 1,2-bis(4-chloro-5H-1,2,3-dithiazol-5-ylidene)hydrazine 4 with benzyltriethylammonium iodide (1 equiv) affords dicyano-1,3,4-thiadiazole 3 and 5-cyano-1,3,4-thiadiazole-2-carboxamide 5 in 79 and 21% yields, respectively. By using polymer bound triphenylphosphine instead of benzyltriethylammonium iodide the dicyano-1,3,4-thiadiazole 3 can be isolated in 70% yield without chromatography. The reaction of DAMN with Appel salt 8 gave 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-2-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)acetonitrile 7 (14%), 2,3-bis-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)fumaronitrile 10 (14%), and 2,3-bis(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)maleonitrile 11 (24%) together with other products. The maleonitrile 11 isomerizes into the fumaronitrile 10 on irradiation at 365 nm. Reaction of aminoacetonitrile with Appel salt 8 gives the (dithiazolylidene)acetonitrile 7 in 33% yield. Treatment of (dithiazolylidene)acetonitrile 7 with polymer bound triphenylphosphine gives tricyanothiazole 6 in 76% yield. A rational general mechanism for the transformation of bisdithiazoles to percyanoheteroles is proposed. © 2009 Elsevier Ltd. All rights reserved. 65 48 9967 9972 Cited By :18 |
| تدمد: |
0040-4020 |
| الوصول الحر: |
https://explore.openaire.eu/search/publication?articleId=doi_dedup___::3908ac19911507c7f595450947728bdeTest
https://doi.org/10.1016/j.tet.2009.10.003Test |
| حقوق: |
OPEN |
| رقم الانضمام: |
edsair.doi.dedup.....3908ac19911507c7f595450947728bde |
| قاعدة البيانات: |
OpenAIRE |
