An investigation of the reaction of 2-aminobenzaldehyde derivatives with conjugated nitro-olefins: An easy and efficient synthesis of 3-nitro-1,2-dihydroquinolines and 3-nitroquinolines

被引：49

作者：

Yan, MC ^{[1
]}

Tu, ZJ ^{[1
]}

Lin, CC ^{[1
]}

Ko, SK ^{[1
]}

Hsu, JM ^{[1
]}

Yao, CF ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 05期

关键词：

D O I：

10.1021/jo030070z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Aryl-3-nitro-1,2-dihydroquinolines 3 were prepared from the reaction of beta-nitrostyrenes 2 and 2-aminobenzaldehyde 1 in the presence of DABCO. Not only beta-nitrostyrenes but other alkyl nitro olefins also can be used in this reaction as well. When DDQ or silica gel was added to a solution of 3-nitro-1,2-dihydroquinolines 3, 3-nitro-2-substituted-quinolines 4 were obtained. When 2-aminobenzaldehyde derivatives 7 and 12 were reacted with beta-nitrostyrenes 2, unique rearrangement products were produced.

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页码：1565 / 1570

页数：6

相关论文

共 47 条

[1] Oxadiazoles as bioisosteric transformations of carboxylic functionalities .2. [J].

Andersen, KE ;

Lundt, BF ;

Jorgensen, AS ;

Braestrup, C .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1996, 31 (05) :417-425

[2] SYNTHESIS OF 4-(2-CHLOROETHYL)-2,3-DIHYDRO[1,4]OXAZINO[2,3-B]QUINOLINE AND 4-(2-CHLOROETHYL)-2,3-DIHYDROPYRIDO[2,3-B][1,4]OXAZINE [J].

ANDERSON, WK ;

DALVIE, DK .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (06) :1533-1536

[3] Direct nitration of pyridine and substituted pyridines [J].

Arnestad, B ;

Bakke, JM ;

Hegbom, I ;

Ranes, E .

ACTA CHEMICA SCANDINAVICA, 1996, 50 (06) :556-557

[4]

BACHARACH G, 1933, RECL TRAV CHIM PAY B, P413

[5]

Bakke JM, 1997, SYNTHESIS-STUTTGART, P281

[6] The synthesis of β-nitropyridine compounds [J].

Bakke, JM ;

Ranes, E ;

Riha, J ;

Svensen, H .

ACTA CHEMICA SCANDINAVICA, 1999, 53 (02) :141-144

[7] CINNOLINES .1. WIDMAN-STOERMER REACTIONS OF FUNCTIONALIZED 2-PHENYLBUT-2-ENES TO GIVE CINNOLINECARBALDEHYDES [J].

BARTON, JW ;

PEARSON, ND .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (07) :1541-1545

[8] SYNTHESIS OF 3-AMINO-2-ARYLQUINOLINES AND 3-NITRO-2-ARYLQUINOLINES [J].

BAUMGARTEN, HE ;

SAYLOR, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (06) :1502-1505

[9] REDUCTIVE MONOALLYLATION OF QUINOLINES AND PHENANTHRIDINE BY TRIALLYLBORANE [J].

BUBNOV, YN ;

EVCHENKO, SV ;

IGNATENKO, AV .

BULLETIN OF THE RUSSIAN ACADEMY OF SCIENCES-DIVISION OF CHEMICAL SCIENCE, 1992, 41 (12) :2239-2240

[10] ALIPHATIC NITRO-COMPOUNDS .1. PREPARATION OF NITRO-OLEFINS BY DEHYDRATION OF 2-NITRO-ALCOHOLS [J].

BUCKLEY, GD ;

SCAIFE, CW .

JOURNAL OF THE CHEMICAL SOCIETY, 1947, (NOV) :1471-1472

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