One-Pot Acid-Catalyzed Ring-Opening/Cyclization/Oxidation of Aziridines with N-Tosylhydrazones: Access to 1,2,4-Triazines

被引：44
|
作者：
Crespin, Lorene [1 ]
Biancalana, Lorenzo [1 ]
Morack, Tobias [1 ]
Blakemore, David C. [2 ]
Ley, Steven V. [1 ]
机构：
[1] Univ Cambridge, Dept Chem, Lensfield Rd, Cambridge CB2 1EW, England
[2] Pfizer Inc, Med Design, Eastern Point Rd, Groton, CT 06340 USA
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 05期
基金：
英国工程与自然科学研究理事会;
关键词：
DIELS-ALDER REACTION; SUBSTITUTED 1,2,4-TRIAZINES; BENZYLIC ALCOHOLS; DERIVATIVES; LANTHANIDES(III); ACTINIDES(III); ANTIBACTERIAL; ALKYLATION; COMPLEXES; PYRIDINES;
D O I：
10.1021/acs.orglett.7b00101
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new, three-step, telescoped reaction sequence for the regioselective conversion of N-tosyl hydrazones and aziridines to 3,6-disubstituted and 3,5,6-trisubstituted 1,2,4-triazines is described. The process involves an efficient nucleophilic ring opening of the aziridine, giving access to a wide range of aminohydrazones, isolated with excellent yields. A "one-pot" procedure, combining the ring opening with a cyclization and an oxidation step, allows the preparation of diversified triazines in good yields.
引用
收藏
页码：1084 / 1087
页数：4
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