Organocatalytic Enantioselective Aminoalkylation of 5-Aminopyrazole Derivatives with Cyclic Imines

被引：13

作者：

Carceller-Ferrer, Laura ^{[1
]}

Gonzalez del Campo, Aleix ^{[1
]}

Vila, Carlos ^{[1
]}

Blay, Gonzalo ^{[1
]}

Munoz, M. Carmen ^{[2
]}

Pedro, Jose R. ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, Dr Moliner 50, Valencia 46100, Spain

[2] Univ Politecn Valencia, Dept Fis Aplicada, Camino Vera S-N, Valencia 46022, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 48期

关键词：

Asymmetric catalysis; Nitrogen heterocycles; Pyrazoles; Organocatalysis; Cyclic imines; CATALYZED NUCLEOPHILIC ALLYLATION; DECARBOXYLATIVE MANNICH REACTION; ASYMMETRIC ARYLATION; ANTIFUNGAL ACTIVITY; INHIBITORS; KETIMINES; CYCLOADDITION; NITROALKANES; ALKYNYLATION; CONSTRUCTION;

D O I：

10.1002/ejoc.202001314

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this communication, an efficient asymmetric aminoalkylation of 5-aminopyrazole derivatives with cyclic benzoxathiazine 2,2-dioxides catalyzed by a quinine-derived squaramide in dichloromethane has been established. This is the first example of 5-aminopyrazole derivatives in asymmetric catalysis. A variety of chiral sulfamidates bearing an aminopyrazole moiety were obtained in good yields (up to 98 %) and moderate to excellent enantioselectivities (up to 99 %ee).

引用

页码：7450 / 7454

页数：5

共 60 条

[1] 5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines [J].

Aggarwal, Ranjana ;

Kumar, Suresh .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 :203-242

[2] Approaches towards the synthesis of 5-aminopyrazoles [J].

Aggarwal, Ranjana ;

Kumar, Vinod ;

Kumar, Rajiv ;

Singh, Shiv P. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :179-197

[3] Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis [J].

Aleman, Jose ;

Parra, Alejandro ;

Jiang, Hao ;

Jorgensen, Karl Anker .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) :6890-6899

[4] Organocatalytic Enantioselective Alkylation of Pyrazol-3-ones with Isatin-Derived Ketimines: Stereocontrolled Construction of Vicinal Tetrasubstituted Stereocenters [J].

Amr, Fares Ibrahim ;

Vila, Carlos ;

Blay, Gonzalo ;

Munoz, M. Carmen ;

Pedro, Jose R. .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (10) :1583-1588

[5] Studies towards the synthesis of Fipronil® analogues:: improved decarboxylation of α-hydrazonoacid derivatives [J].

Ancel, JE ;

El Kaïm, L ;

Gadras, A ;

Grimaud, L ;

Jana, NK .

TETRAHEDRON LETTERS, 2002, 43 (46) :8319-8321

[6]

[Anonymous], 2012, ANGEW CHE

[7] Recent developments in aminopyrazole chemistry [J].

Anwar, Hany Fakhry ;

Elnagdi, Mohamed Hilmy .

ARKIVOC, 2009, :198-250

[8] Organocatalytic enantioselective aminoalkylation of pyrazol-3-ones with aldimines generated in situ from α-amido sulfones [J].

Carceller-Ferrer, Laura ;

Vila, Carlos ;

Blay, Gonzalo ;

Fernandez, Isabel ;

Carmen Munoz, M. ;

Pedro, Jose R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (46) :9859-9863

[9] Inhibition of drug-resistant mutants of ABL, KIT, and EGF receptor kinases [J].

Carter, TA ;

Wodicka, LM ;

Shah, NP ;

Velasco, AM ;

Fabian, MA ;

Treiber, DK ;

Milanov, ZV ;

Atteridge, CE ;

Biggs, WH ;

Edeen, PT ;

Floyd, M ;

Ford, JM ;

Grotzfeld, RM ;

Herrgard, S ;

Insko, DE ;

Mehta, SA ;

Patel, HK ;

Pao, W ;

Sawyers, CL ;

Varmus, H ;

Zarrinkar, PP ;

Lockhart, DJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2005, 102 (31) :11011-11016

[10] 5-Amino-pyrazoles as potent and selective p38α inhibitors [J].

Das, Jagabandhu ;

Moquin, Robert V. ;

Dyckman, Alaric J. ;

Li, Tianle ;

Pitt, Sidney ;

Zhang, Rosemary ;

Shen, Ding Ren ;

McIntyre, Kim W. ;

Gillooly, Kathleen ;

Doweyko, Arthur M. ;

Newitt, John A. ;

Sack, John S. ;

Zhang, Hongjian ;

Kiefer, Susan E. ;

Kish, Kevin ;

McKinnon, Murray ;

Barrish, Joel C. ;

Dodd, John H. ;

Schieven, Gary L. ;

Leftheris, Katerina .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (23) :6886-6889

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