2015
DOI: 10.1021/acscombsci.5b00140
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A Highly Efficient Diversification of 2-Amino/Amido-1,3,4-oxadiazole and 1,3,4-Thiadiazole Derivatives via Reagent-Based Cyclization of Thiosemicarbazide Intermediate on Solid-Phase

Abstract: A 2-amino/amido-1,3,4-oxadiazole and 1,3,4-thiadiazole library has been constructed on solid-phase organic synthesis. The key step on this solid-phase synthesis involves the preparation of polymer-bound 2-amino-1,3,4-oxadiazole and 1,3,4-thiadiazole core skeleton resin by cyclization of thiosemicarbazide with EDC·HCl and p-TsCl, respectively. The resulting core skeleton undergoes functionalization reaction with various electrophiles such as alkyl halides, and acid chlorides to generate N-alkylamino and N-acyla… Show more

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Cited by 27 publications
(17 citation statements)
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“…1 . The previous methods for the synthesis of 2-acylamino-1,3,4-oxadiazoles: ( a ) Two-step procedure to synthesize 2-acylamino-1,3,4-oxadiazoles by cyclization and amidization [22,23,24,25,26,27,28,29,30,31,32,33,34,35]; ( b ) One-step procedure to synthesize 2-acylamino-1,3,4-oxadiazoles by desulfurated cyclization [11,36,37,38,39,40,41]. 2 .…”
Section: Figure Schemes and Tablesmentioning
confidence: 99%
See 1 more Smart Citation
“…1 . The previous methods for the synthesis of 2-acylamino-1,3,4-oxadiazoles: ( a ) Two-step procedure to synthesize 2-acylamino-1,3,4-oxadiazoles by cyclization and amidization [22,23,24,25,26,27,28,29,30,31,32,33,34,35]; ( b ) One-step procedure to synthesize 2-acylamino-1,3,4-oxadiazoles by desulfurated cyclization [11,36,37,38,39,40,41]. 2 .…”
Section: Figure Schemes and Tablesmentioning
confidence: 99%
“…To date, different methods have been developed for the synthesis of these heterocyles. The most straightforward synthesis relies on the cyclization of corresponding thiosemicarbazide derivatives with several desulfurating agents [22], such as 1,3-dibromo-5,5-dimethylhydantoin [23]; p -tosyl chloride [24,25]; alkylating agents [26,27], such as methyl iodide and ethyl bromoacetate; carbodiimides [28,29]; mercury (II) acetate [30,31,32]; oxone [33]; and POCl 3 [34] (Scheme 1).…”
Section: Introductionmentioning
confidence: 99%
“…[18] Seung et al synthesized oxadiazole derivatives by employing solid phase synthetic strategy via thiosemicarbazide desulfurization using various reagents. [19] Frank et al used various resin-bound reagents for the synthesis of 5-substituted-2-amino-1,3,4-oxadiazoles. [20] In recent years, molecular iodine, IBX and carbodiimide reagents have been used for these transformations (Scheme 1).…”
Section: Introductionmentioning
confidence: 99%
“…Seung et al . synthesized oxadiazole derivatives by employing solid phase synthetic strategy via thiosemicarbazide desulfurization using various reagents [19] . Frank et al .…”
Section: Introductionmentioning
confidence: 99%
“…The acylthiosemi carbazide was annulated following a desulfurative cyclization giving the 2-amino substituted oxadiazole (30). Complete regioselectivity for the 1,3,4-oxadiazole instead of the thiodiazole was gotten when annulation of the thiosemicarbazide was carried out with EDC.HCl in DMSO instead of p-TsCl/TEA, which gave moderate to high regioselectivity depending on the electron-withdrawing/donating nature of the R1 group49 .Scheme 27. Solid-phase cyclodesulphurization of thiosemicarbazide Following a similar route as Yang and co-workers, the desulfuration of hydrazinecarbothioamide resin (31) using p-TsCl and pyridine in THF resulted in cyclization to the required 1,3,4-oxadiazole (32) as shown in Scheme 28 50 .…”
mentioning
confidence: 99%