Synthesis of 5(6H)-phenanthridones using Diels-Alder reaction of 3-nitro-2(1H)-quinolones acting as dienophiles

被引：19

作者：

Fujita, R ^{[1
]}

Yoshisuji, T ^{[1
]}

Wakayanagi, S ^{[1
]}

Wakamatsu, H ^{[1
]}

Matsuzaki, H ^{[1
]}

机构：

[1] Tohoku Pharmaceut Univ, Aoba Ku, Sendai, Miyagi 9818558, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2006年 / 54卷 / 02期

关键词：

3-nitro-2(1H)quinolone; Diels-Alder reaction; 6(5H)-phenanthridone; 1-methoxy-1,3-butadiene; 2,3-dimethoxy1,3-butadiene; molecular orbital (MO) calculation;

D O I：

10.1248/cpb.54.204

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Diels-Alder reactions of 3-nitro-2(1H)-quinolones with 1,3-butadiene derivatives were carried out to give the phenanthridone derivatives under both atmospheric and high pressure conditions. Furthermore, the reactivity of 3-substituted 2(1H)-quinolones acting as a dienophile with 2,3-dimethyl-1,3-butadiene was examined using molecular orbital (MO) calculation.

引用

页码：204 / 208

页数：5

共 28 条

[1] 6-chloro-spirocyclohexenindol-2-ones: an unusual ring transformation to ethyl 2-(cyclohexa-1,4-dienyl)phenylcarbamates. [J].

Beccalli, EM ;

Clerici, F ;

Gelmi, ML .

TETRAHEDRON, 1999, 55 (28) :8579-8586

[2] NARCICLASINE - AN ANTIMITOTIC SUBSTANCE FROM NARCISSUS BULBS [J].

CERIOTTI, G .

NATURE, 1967, 213 (5076) :595-&

[3] BROMINATION STUDIES OF ALKYL-SUBSTITUTED 2-PYRIDONES AND 2-QUINOLONES [J].

COOK, DJ ;

SORTER, P ;

DANIELS, E ;

BOWEN, RE .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (12) :4949-&

[4]

Frisch M.J., 2016, Gaussian 16 Revision C. 01. 2016, V01

[5] Novel Diels-Alder reaction of 4-nitro-1(2H)-isoquinolones [J].

Fujita, R ;

Wakayanagi, S ;

Wakamatsu, H ;

Matsuzaki, H .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (02) :209-212

[6]

Fujita R, 2003, CHEM PHARM BULL, V51, P295

[7] Diels-Alder cycloadditions of 2(1H)-quinolones having an electron withdrawing group at the 3-position acting as dienophiles with dienes [J].

Fujita, R ;

Watanabe, K ;

Yoshisuji, T ;

Kabuto, C ;

Matsuzaki, H ;

Hongo, H .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (07) :893-899

[8] Diels-Alder reaction of 1,3-butadiene derivatives with 1-methyl-2(1H)quinolones having an electron-withdrawing group at the 4-position [J].

Fujita, R ;

Watanabe, K ;

Yoshisuji, T ;

Hongo, H ;

Matsuzaki, H .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (07) :900-904

[9] Synthesis of phenanthridones using Diels-Alder reactions of 4-substituted 2(1H)-quinolones acting as dienophiles [J].

Fujita, R ;

Watanabe, K ;

Yoshisuji, T ;

Matsuzaki, H ;

Harigaya, Y ;

Hongo, H .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (04) :407-412

[10] Synthesis of trisphaeridine and norchelerythrine through palladium-catalyzed aryl-aryl coupling reaction [J].

Harayama, T ;

Akamatsu, H ;

Okamura, K ;

Miyagoe, T ;

Akiyama, T ;

Abe, H ;

Takeuchi, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (05) :523-528

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