Unexpected regiochemistry in [3+2] cycloaddition reaction of azomethine ylides of indenoquinoxalinone series to arylidene malononitriles

被引：14

作者：

Barkov, Alexey Yu ^{[1
]}

Zimnitskiy, Nikolay S. ^{[1
]}

Kutyashev, Igor B. ^{[1
]}

Korotaev, Vladislav Yu ^{[1
]}

Sosnovskikh, Vyacheslav Ya ^{[1
]}

机构：

[1] Ural Fed Univ, Inst Nat Sci & Math, 51 Lenina Ave, Ekaterinburg 620000, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2018年 / 54卷 / 01期

关键词：

arylidene malononitriles; indenoquinoxalinones; spiropyrrolidines; spiropyrrolizidines; stabilized azomethine ylides; 1,3-dipolar cycloaddition; STEREOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; IONIC LIQUID; SPIRO-PYRROLIDINE; MULTICOMPONENT; DERIVATIVES; HETEROCYCLES; PYRROLIZIDINES; INHIBITORS; EFFICIENT; NINHYDRIN;

D O I：

10.1007/s10593-018-2228-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar cycloaddition of azomethine ylides generated in situ from proline and indenoquinoxalinones occurred at the double bond of arylidene malononitriles upon heating in isopropanol, leading to the respective spirocyclic adducts with cis orientation of the aryl substituent and the quinoxaline moiety. The regioselectivity of this process depended on the electron donor-acceptor properties of substituents in the aromatic ring of the dipolarophile molecule. Analogous reaction involving azomethine ylide derived from sarcosine produced adducts with a trans relationship of the most sterically demanding substituents.

引用

页码：43 / 50

页数：8

共 36 条

[1] An expedient microwave assisted regio-and stereoselective synthesis of spiroquinoxaline pyrrolizine derivatives and their AChE inhibitory activity [J].

Akondi, Adinarayana Murthy ;

Mekala, Sowmya ;

Kantam, Mannepalli Lakshmi ;

Trivedi, Rajiv ;

Chowhan, L. Raju ;

Das, Amitava .

NEW JOURNAL OF CHEMISTRY, 2017, 41 (02) :873-878

[2] An experimental and theoretical investigation of the regio- and stereoselectivity of the polar [3+2] cycloaddition of azomethine ylides to nitrostyrenes [J].

Alimohammadi, Kamal ;

Sarrafi, Yaghoub ;

Tajbakhsh, Mahmood ;

Yeganegi, Saeed ;

Hamzehloueian, Mahshid .

TETRAHEDRON, 2011, 67 (08) :1589-1597

[3] A facile synthesis of novel ferrocene grafted spiro-indenoquinoxaline pyrrolizidines via one-pot multicomponent [3+2] cycloaddition of azomethine ylides [J].

Babu, A. R. Suresh ;

Gavaskar, D. ;

Raghunathan, R. .

TETRAHEDRON LETTERS, 2012, 53 (49) :6676-6681

[4] Regio- and stereoselective 1,3-dipolar cycloaddition of indenoquinoxalinone azomethine ylides to β-nitrostyrenes: synthesis of spiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizidines] and spiro[indeno[1,2-b]quinoxaline-11,2′-pyrrolidines] [J].

Barkov, Aleksey Yi. ;

Zimnitskiy, Nikolay S. ;

Korotaev, Vladislav Yu. ;

Kutyashev, Igor B. ;

Moshkin, Vladimir S. ;

Sosnovskikh, Vyacheslav Ya. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (04) :451-459

[5] Regio- and stereoselective 1,3-dipolar cycloaddition reactions between arylideneacetones and stabilized azomethine ylides obtained from ninhydrin and indenoquinoxalinones [J].

Barkov, Alexey Yu. ;

Zimnitskiy, Nikolay S. ;

Kutyashev, Igor B. ;

Korotaev, Vladislav Yu. ;

Sosnovskikh, Vyacheslav Ya. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (12) :1315-1323

[6] Highly regio- and stereoselective 1,3-dipolar cycloaddition of stabilised azomethine ylides to 3,3,3-trihalogeno-1-nitropropenes: Synthesis of trihalomethylated spiroindenepyrroli(zi)dines [J].

Barkov, Alexey Yu. ;

Zimnitskiy, Nikolay S. ;

Kutyashev, Igor B. ;

Korotaev, Vladislav Yu. ;

Moshkin, Vladimir S. ;

Sosnovskikh, Vyacheslav Ya. .

JOURNAL OF FLUORINE CHEMISTRY, 2017, 204 :37-44

[7] Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines [J].

Buev, Evgeny M. ;

Moshkin, Vladimir S. ;

Sosnovskikh, Vyacheslav Y. .

ORGANIC LETTERS, 2016, 18 (08) :1764-1767

[8] Ultrasound-promoted regioselective and stereoselective synthesis of novel spiroindanedionepyrrolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides [J].

Chandralekha, Elangovann ;

Thangamani, Arumugam ;

Valliappan, Ramiah .

RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (03) :961-972

[9] Synthesis and regiochemistry of spiro indane-1,3-dione compounds [J].

Chen, Gang ;

Zhang, Jie ;

Wu, Ya .

RESEARCH ON CHEMICAL INTERMEDIATES, 2012, 38 (02) :413-420

[10] A CuII-N,P Oxazolinylferrocene Ligand Complex for the Asymmetric [3+2] 1,3-Dipolar Cycloaddition of Azomethine Ylide with Malonates [J].

Dai, Li ;

Xu, Di ;

Tang, Li-Wei ;

Zhou, Zhi-Ming .

CHEMCATCHEM, 2015, 7 (07) :1078-1082

← 1 2 3 4 →