Synthesis of New Functionalized 2-Alkylsulfanyl-5-(1H-indol-2-yl)-1,3,4-Oxadiazole and a Facile Thio-Aza-Claisen Rearrangement of the S-Allyl Analog

被引：10
作者：
El Ashry, El Sayed H. [1 ]
El Tamany, El Sayed H. [2 ]
El Fattah, Mohy El Din Abd [2 ]
Aly, Mohamed R. E. [3 ]
Boraei, Ahmed T. A. [1 ]
机构：
[1] Univ Karachi, Int Ctr Chem & Biol Sci, HEJ Res Inst Chem, Karachi 75270, Pakistan
[2] Suez Canal Univ, Fac Sci, Dept Chem, Ismailia, Egypt
[3] Suez Canal Univ, Fac Sci Appl, Dept Chem, Port Said, Egypt
来源：
LETTERS IN ORGANIC CHEMISTRY | 2009年 / 6卷 / 06期
关键词：
Indoles; oxadiazoles; indolyloxadiazoles; thio-aza-Claisen rearrangement; allylic rearrangement; ANTIVIRAL EVALUATION; SCHIFF-BASES; DERIVATIVES; INHIBITORS;
D O I：
10.2174/157017809789124902
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The S-alkylated indolyloxadiazoles 2a-1 were obtained regioselectively by alkylation of 5-(1H-indol-2-yl)-1,3,4- oxadiazole-2(3H)-thione 1, using TEA as acid scavenger. Alkylation of 1 with 1-bromopropane, 1-bromobutane, 1bromoundecan, in the presence of K2CO3, yielded the N-alkylated products 3i-j, m in addition to the S-alkylated analogs 2i-j, m. A facile thio-aza-Claisen rearrangement (S -> N allylic rearrangement) of the S-allyl-oxadiazole 2k to the N-allyl analog 3k was achieved in excellent yield. Further allylation of 2k and 3k in the presence of K2CO3 led to allylation of the NH indole ring producing 5 and 6, respectively. Benzylation of 1 in the presence of K2CO3 yielded 7 which resisted the S -> N migration of the benzyl group. The H-1 NMR, C-13 NMR and mass spectra confirmed the structures and differentiated between the N- and S-alkylated products.
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收藏
页码：462 / 469
页数：8
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