1,3,4-Oxadiazole and Heteroaromatic-Fused 1,2,4-Triazole Synthesis using Diverted Umpolung Amide Synthesis.
1,3,4-Oxadiazole and Heteroaromatic-Fused 1,2,4-Triazole Synthesis using Diverted Umpolung Amide Synthesis.
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DOI：
10.1055/s-0036-1590802
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发表时间：
2017-10
期刊：
影响因子：
--
通讯作者：
Johnston JN
中科院分区：
文献类型：
--
作者：
Tokumaru K;Bera K;Johnston JN
Umpolung Amide Synthesis (UmAS) has emerged as a superior alternative to conventional amide synthesis methods based on carbonyl electrophiles in a range of situations, particularly when epimerization-prone couplings are prescribed. In an unanticipated development during our most recent studies, it was discovered that diacyl hydrazide products from UmAS were not formed as intermediates when using an acyl hydrazide as the amine acceptor. This resulted in a new preparation of 1,3,4-oxadiazoles from α-bromonitroalkane donors. We hypothesized that a key tetrahedral intermediate in UmAS was diverted toward a more direct pathway to the heterocycle product rather than through formation of the diacyl hydrazide, a typical oxadiazole progenitor. In studies reported here, diversion to 1,2,4-triazole products is described, a behavior hypothesized to also result from an analogous tetrahedral intermediate, but one formed from heteroaromatic hydrazine acceptors.
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影响因子：
12.9
作者：
Schwieter KE;Johnston JN
通讯作者：
Johnston JN
DOI：
10.1039/c39860000658
发表时间：
1986-05-01
影响因子：
--
作者：
AMIN, MR;DEKKER, L;SANDALL, JPB
通讯作者：
SANDALL, JPB
影响因子：
1.1
作者：
HARTSHORN, MP;ROBINSON, WT;CHENG, LY
通讯作者：
CHENG, LY
影响因子：
64.8
作者：
通讯作者：
--
影响因子：
2.1
作者：
Dong, Li-ting;Lu, Rui-jiong;Yan, Ming
通讯作者：
Yan, Ming