An efficient and convenient method for synthesizing new derivatives of pyrido[2,3-e]pyrrolo[1,2-a][1,4]diazepine-5,10-dione via Sonogashira, Suzuki-Miyaura, and Stille cross-coupling reactions

被引：5

作者：

El Bouakher, Abderrahman ^{[1
]}

Prie, Gildas

Aadil, Mina ^{[1
]}

Lazar, Said ^{[1
]}

El Hakmaoui, Ahmed ^{[1
]}

Akssira, Mohamed ^{[1
]}

Viaud-Massuard, Marie-Claude

机构：

[1] Univ Hassan II Mohammedia Casablanca, URAC 22, Lab Chim Bioorgan & Analyt, Mohammadia 20800, Morocco

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 47期

关键词：

2-Aminonicotinic acid; (S)-3-Bromo-7,8,9,9a-tetrahydro-5H-pyrido[2,3e]pyrrolo[1,2a][1,4]diazepine-5,10(11H)-dione; C-C Cross-coupling reactions; PYRROLO<1,4>BENZODIAZEPINE ANTIBIOTICS; BOND FORMATION; COPPER-FREE; ANTHRAMYCIN; SIBIROMYCIN; TOMAYMYCIN;

D O I：

10.1016/j.tetlet.2012.09.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for synthesizing new pyrido[2,3-e]pyrrolo[1,2-a][1,4]diazepine-5,10-dione derivatives starting from L-proline methyl ester and 2-aminonicotinic acid is presented. This method employs Pd-catalyzed cross-coupling reaction on the corresponding brominated compound 4 (key intermediate). Sonogashira, Stille, and Suzuki-Miyaura cross-coupling reactions are used to generate products 5a-g, 6, 7a-c, and 8a-e, in good to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：6401 / 6405

页数：5

共 13 条

[1] Regiocontrolled functionalization of 2,3-dihalogenoimidazo[1,2-a] pyridines by Suzuki-Miyaura and Sonogashira cross-coupling reactions
Delaye, P. -O.
Penichon, M.
Allouchi, H.
Enguehard-Gueiffier, C.
Gueiffier, A.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (19) : 4199 - 4204
[2] Suzuki-Miyaura cross-coupling reactions of halo derivatives of 4H-pyrido[1,2-a]pyrimidin-4-ones
Molnar, Annamaria
Kapros, Anita
Parkanyi, Laszlo
Mucsi, Zoltan
Vlad, Gabor
Hermecz, Istvan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) : 6559 - 6565
[3] A novel and convenient method for the synthesis of new derivatives of pyrido[3,2-e]pyrrolo[1,2-a][1,4]diazepine-6,11-dione
El Bouakher, Abderrahman
Prie, Gildas
Aadil, Mina
Lazar, Said
Akssira, Mohamed
Viaud-Massuard, Marie-Claude
TETRAHEDRON, 2012, 68 (47) : 9572 - 9577
[4] Synthesis of new 4-(E)-alkenylpyrrolo[1,2-a]quinoxalines as antileishmanial agents by Suzuki-Miyaura cross-coupling reactions
Guillon, Jean
Forfar, Isabelle
Desplat, Vanessa
Fabre, Solene Belisle
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Carrie, Helene
Mossalayi, Djavad
Jarry, Christian
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2007, 22 (05) : 541 - 549
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Tber, Zahira
Biteau, Nicolas G.
Agrofoglio, Luigi
Cros, Julien
Goffinont, Stephane
Castaing, Bertrand
Nicolas, Cyril
Roy, Vincent
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (33) : 5756 - 5767
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Kabri, Youssef
Crozet, Maxime D.
Szabo, Remi
Vanelle, Patrice
SYNTHESIS-STUTTGART, 2011, (19): : 3115 - 3122
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El-Kashef, HS
El-Dean, AMK
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Lancelot, JC
Dallemagne, P
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JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (06) : 1521 - 1526
[8] Synthesis of pyrazino[2,3-e][1,4]diazepin-5-one and pyrazino[2,3-e]pyrrolo[1,2-a][1,4]diazepin-5-one derivatives via the intramolecular aza-Witting reaction
Okawa, T
Eguchi, S
TETRAHEDRON, 1998, 54 (22) : 5853 - 5868
[9] 10,10′-Methylenebis[2,3-dihydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-5,11(10H,11aH)-dione] dihydrate
Benzeid, Hanane
Saffon, Nathalie
Garrigues, Bernard
Essassi, El Mokhtar
Ng, Seik Weng
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O2684 - U211
[10] Synthesis of Pyrazino[2,3-e][1,4]diazepin-5-one and Pyrazino[2,3-e]pyrrolo[1,2-a][1,4]diazepin-5$ MIN@one Derivatives via the Intramolecular Aza-Wittig Reaction
Tetrahedron, 22 (5853):

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