Zn-catalyzed hydrohydrazination of propargylamides with BocNHNH2: a novel entry into the 1,2,4-triazine core

被引：16

作者：

Lukin, Alexey ^{[1
]}

Vedekhina, Tatiana ^{[1
]}

Tovpeko, Dmitry ^{[1
]}

Zhurilo, Nikolay ^{[1
]}

Krasavin, Mikhail ^{[2
]}

机构：

[1] Moscow Technol Univ, Lomonosov Inst Fine Chem Tehnol, 86 Vernadskogo Prospekt, Moscow 117571, Russia

[2] St Petersburg State Univ, St Petersburg 199034, Russia

来源：

RSC ADVANCES | 2016年 / 6卷 / 63期

基金：

俄罗斯科学基金会;

关键词：

AS-TRIAZINE DERIVATIVES; SUBSTITUTED 1,2,4-TRIAZINES; TERMINAL ALKYNES; FACILE SYNTHESIS; COMPLEXES; CYCLOADDITIONS; PYRIMIDINES; OXIDATION; PYRAZINES; AGENTS;

D O I：

10.1039/c6ra12664b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hydrohydrazination of a variety of propargylamides with BocNHNH(2) under Zn(OTf)(2) catalysis, unexpectedly, gave dihydro-1,2,4-triazines with a loss of the protecting group. The initial products can be efficiently aromatized in situ with K-3[Fe(CN)(6)]. This provides a new entry into the medicinally important 1,2,4-triazine core.

引用

页码：57956 / 57959

页数：4

共 36 条

[1] Adam G., 2003, PCT Int. Appl., Patent No. [2003066623, WO 2003066623A1]
[2] Synthesis of substituted fused pyridines, pyrazines and pyrimidines by sequential Ugi/inverse electron demand Diels-Alder transformations
Akritopoulou-Zanze, Irini
Wang, Ying
Zhao, Hongyu
Djuric, Stevan W.
[J]. TETRAHEDRON LETTERS, 2009, 50 (42) : 5773 - 5776
[3] Zinc-promoted hydrohydrazination of terminal alkynes: An efficient domino synthesis of indoles
Alex, Karolin
Tillack, Annegret
Schwarz, Nicolle
Beller, Matthias
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) : 2304 - 2307
[4] SYNTHESIS AND ANTI-INFLAMMATORY ACTIVITY OF TRISUBSTITUTED PYRIMIDINES AND TRIAZINES
BENNETT, GB
MASON, RB
ALDEN, LJ
ROACH, JB
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (07) : 623 - 628
[5] Bruce D. W., 2010, PCT Int. Appl., Patent No. [WO 2010112799A1, 2010112799]
[6] Synthesis and pharmacological evaluation of phenylethynyl[1,2,4]methyltriazines as analogues of 3-methyl-6-(phenylethynyl)pyridine
Carroll, F. Ivy
Kotturi, Sharadsrikar V.
Navarro, Hernan A.
Mascarella, S. Wayne
Gilmour, Brian P.
Smith, Forrest L.
Gabra, Bichoy H.
Dewey, William L.
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (14) : 3388 - 3391
[7] Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines
Coogan, Niall T.
Chimes, Michael A.
Raftery, James
Mocilac, Pavle
Denecke, Melissa A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17) : 8684 - 8693
[8] Learning from our mistakes: The 'unknown knowns' in fragment screening
Davis, Ben J.
Erlanson, Daniel A.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (10) : 2844 - 2852
[9] Introduction to Fragment-Based Drug Discovery
Erlanson, Daniel A.
[J]. FRAGMENT-BASED DRUG DISCOVERY AND X-RAY CRYSTALLOGRAPHY, 2012, 317 : 1 - 32
[10] Cycloadditions of aryl-substituted 1,2,4-triazines with 2-cyclopropylidene-1,3-dimethylimidazolidine - Zwitterions as discrete intermediates
Ernd, M
Heuschmann, M
Zipse, H
[J]. HELVETICA CHIMICA ACTA, 2005, 88 (06) : 1491 - 1518

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