Directed synthesis of new spiro-fused photochromes of diarylethene series

被引：23

作者：

Belikov, Mikhail Yu. ^{[1
]}

Ievlev, Mikhail Yu. ^{[1
]}

Belikova, Irina V. ^{[1
]}

Ershov, Oleg V. ^{[1
]}

Tafeenko, Viktor A. ^{[2
]}

Surazhskaya, Marina D. ^{[3
]}

机构：

[1] Chuvash State Univ, Cheboksary 428015, Russia

[2] Moscow MV Lomonosov State Univ, Moscow 119991, Russia

[3] NS Kurnakov Inst Gen & Inorgan Chem, Moscow 119991, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2015年 / 51卷 / 06期

关键词：

1,2-diarylethanones; diarylethenes; tetracyanoethylene; ethene linker; non-bonded strain; photochromes; spiro compounds; spirofusion; tetracyanoethylation; CLOSED-RING ISOMER; CYCLOPENTENONE SERIES; THERMAL-STABILITY; DERIVATIVES; SWITCHES; 4-ARYL-4-OXOBUTANE-1,1,2,2-TETRACARBONITRILES; PERFORMANCE; ELECTRONICS; MOLECULES; MEMORIES;

D O I：

10.1007/s10593-015-1731-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of tetracyanoethylated 1,2-diarylethanones with morpholine was used for directed synthesis of spiro-fused diarylethenes, 8-amino-1-imino(oxo)-6-morpholino-2-oxa-7-azaspiro[4.4]nona-3,6,8-triene-9-carbonitriles. The intermediates in this process were tetracyanoalkanone salts. The formation of spiranes was sensitive to the nature of aromatic substituents at the carbonyl group of 3,4-diaryl-4-oxobutane-1,1,2,2-tetracarbonitriles. The obtained spiro-fused diarylethenes exhibited photochromic properties.

引用

收藏

页码：518 / 525

页数：8

相关论文

共 47 条

[1] Synthesis of photochromic 5,6-diaryl-2-chloropyridine-3,4-dicarbonitriles from 3,4-diaryl-4-oxobutane-1,1,2,2-tetracarbonitriles [J].

Belikov, M. Yu. ;

Ievlev, M. Yu. ;

Ershov, O. V. ;

Lipin, K. V. ;

Legotin, S. A. ;

Nasakin, O. E. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (09) :1372-1374

[2] Hydrolysis and acylation of imino group in E/Z-isomers of 3,4-dialkyl-8-amino-1-imino-6-morpholin-4-yl-2-oxa-7-azaspiro[4.4]nona-3,6,8-triene-9-carbonitriles [J].

Belikov, M. Yu. ;

Ershov, O. V. ;

Lipovskaya, I. V. ;

Fedoseev, S. V. ;

Lipin, K. V. ;

Nasakin, O. E. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (08) :1195-1198

[3] Spiro heterocyclization of 4-aryl-4-oxobutane-1,1,2,2-tetracarbonitriles to 3H-pyrrole derivatives, 2-oxa-7-azaspiro[4.4]nona-3,6,8-trienes [J].

Belikov, M. Yu ;

Ershov, O. V. ;

Lipovskaya, I. V. ;

Fedoseev, S. V. ;

Nasakin, O. E. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (06) :864-866

[4] Reaction between 4-oxoalkane-1,1,2,2-tetracarbonitriles and morpholine: regioselective synthesis of 5-amino-2-(morpholin-4-yl)-3-(2-oxoalkyl)-3H-pyrrol-3,4-dicarbonitriles [J].

Belikov, M. Yu. ;

Ershov, O. V. ;

Eremkin, A. V. ;

Nasakin, O. E. ;

Tafeenko, V. A. ;

Nurieva, E. V. .

TETRAHEDRON LETTERS, 2011, 52 (48) :6407-6410

[5] Synthesis of 5-amino-3H-pyrrole-3,4-dicarbonitriles from 4-aryl-4-oxobutane-1,1,2,2-tetracarbonitriles [J].

Belikov, M. Yu. ;

Ershov, O. V. ;

Lipovskaya, I. V. ;

Eremkin, A. V. ;

Nasakin, O. E. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (09) :1426-1427

[6] Synthesis of a new organic anion by reaction of 4-aryl(hetaryl)-4-oxobutane-1,1,2,2-tetracarbonitriles with ammonia [J].

Belikov, M. Yu. ;

Ershov, O. V. ;

Eremkin, A. V. ;

Kayukov, Ya. S. ;

Nasakin, O. E. .

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (04) :597-598

[7] Polymeric networks of silver(I) and copper(I) ions linked by an anionic acetonyl derivative of tetracyanoethylene [J].

Carlucci, L ;

Ciani, G ;

Proserpio, DM ;

Sironi, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (10) :1088-1090

[8] WHAT HAPPENS DURING THE PICOSECOND LIFETIME OF 2A(1) CYCLOHEXA-1,3-DIENE - A CAS-SCF STUDY OF THE CYCLOHEXADIENE HEXATRIENE PHOTOCHEMICAL INTERCONVERSION [J].

CELANI, P ;

OTTANI, S ;

OLIVUCCI, M ;

BERNARDI, F ;

ROBB, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) :10141-10151

[9] Synthesis and photochromic properties of functional diarylethene with a 2,5-dihydrothiophene bridging unit [J].

Chen, Y ;

Zeng, DX ;

Fan, MG .

ORGANIC LETTERS, 2003, 5 (09) :1435-1437

[10] Synthesis and in vitro activity of 6-amino-2,9-diarylpurines for Mycobacterium tuberculosis [J].

Correia, Carla ;

Carvalho, M. Alice ;

Proenca, M. Fernanda .

TETRAHEDRON, 2009, 65 (34) :6903-6911

← 1 2 3 4 5 →