Anionic cascade recyclization of pyrazolo[5,1-c][1,2,4]triazines to pyrrolo[1,2-b][1,2,4]triazine and [1,2,4]triazino[2′,3′:1,5]pyrrolo [3,2-c]isoquinoline systems

被引：12
|
作者：
Ivanov, Sergey M. [1 ,2 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Leninsky Prospekt 47, Moscow 119991, Russia
[2] DI Mendeleev Univ Chem Technol Russia, Miusskaya Ploshchad 9, Moscow 125047, Russia
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 42期
关键词：
1,2,4-triazine; Pyrazolo[5,1-c][1,2,4]triazine; Pyrrolo[1,2-b][1,2,4]triazine; Lithiation; X-ray diffraction; ELECTROPHILIC SUBSTITUTION; DERIVATIVES; TRIAZINES; NITROGEN;
D O I：
10.1016/j.tetlet.2020.152404
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The treatment of tert-butyl 2-(7-bromo-3-tert-butyl-8-R-4-oxopyrazolo[5,1-c][1,2,4]triazin-1(4H)-yl)acetates (R = CN, CO2Et, NO2) with alkyl lithiums in THF at low temperature led to rapid cascade reactions with the formation of tert-butyl 7-amino-3-tert-butyl-8-R-2-oxo-1,2-dihydropyrrolo[1,2-b][1,2,4]triazine-6-carboxylates in high yields. However, only an inert 1,2,4-triazinone was isolated in the case of R = Me. A tetracyclic [1,2,4]triazino[2',3':1,5]pyrrolo[3,2-c]isoquinoline derivative was also formed via recyclization of the appropriately functionalized substrate. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：5
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