One-step Synthesis of Dialkyl 1,2-Dihydroquinoline-2,3-dicarboxylates. A Vinyltriphenylphosphonium Salt Mediated Intramolecular Wittig Reaction†

Yavari, Issa; Ramazani, Ali; Esmaili, Abbas Ali

doi:10.1039/a608156h

Cited by 33 publications

(26 citation statements)

References 11 publications

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“…[8][9][10] Similar reactions can be achieved from indole-7-carbaldehydes, and a six-membered ring is fused between C7 and N1, to give pyrroloquinolines. In the case of a 6-hydroxy-7-formylindole, there is a choice of reaction between the indole nitrogen and the phenolic oxygen atoms.…”

Section: Cyclisation Between C7 and N1 On The Indole Ringmentioning

confidence: 88%

Augmented indoles

Black¹,

Channon²,

Clayton³

et al. 2006

Arkivoc

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The indole ring presents a good platform for synthesis because of its nucleophilic capacity at C3, to a lesser extent at C2, and also through the indole anion at N1. The development of new indoles with strategically placed methoxy groups at C4 and C6, or C5 and C7, provides even better platforms not only through increased general activation, but also through specific activation at C7 and C4 respectively. As a result of this multi-faceted activity, it is possible to generate a variety of additional rings fused to the indole platform. This rather general strategy of molecular augmentation leads to new types of indole structures, some of which bear resemblance to natural indole alkaloids. A selection of examples is presented.

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Section: Cyclisation Between C7 and N1 On The Indole Ringmentioning

confidence: 88%

Augmented indoles

Black¹,

Channon²,

Clayton³

et al. 2006

Arkivoc

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“…Quinoline derivatives are important heterocycles in bio-organic chemistry and are present in many natural products and pharmaceuticals [1]. In recent years there has been increasing interest in the determination of X-ray crystal structures of biologically active compounds [2][3][4][5][6][7][8].…”

Section: Discussionmentioning

confidence: 99%

“…Dimethyl 1-acetyl-1,2-dihydro-2,3-quinolinedicarboxylate, was synthesized in accordance with the published procedure [1]. Single crystals were prepared in n-hexane at 322 K during five weeks using the branch tube method.…”

Section: Source Of Materialsmentioning

confidence: 99%

Crystal structure of dimethyl 1-acetyl-1,2-dihydro-2,3-quinolinedicarboxylate, C15H15NO5

Ramazani

Dolatyari

Kazemizadeh

et al. 2004

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialDimethyl 1-acetyl-1,2-dihydro-2,3-quinolinedicarboxylate, was synthesized in accordance with the published procedure [1]. Single crystals were prepared in n-hexane at 322 K during five weeks using the branch tube method. The colorless crystals were filtered off, washed with cold n-hexane (5 ml) and dried in vacuum over P 4O10 (m.p. 411 K). Elemental analyses were consistent with the composition C 15 H 15 NO 5 (found: C, 62.21 %; H, 5.19 %; N, 4.91 %; calc.: C, 62.28 %; H, 5.23 %; N, 4.84 %). Melting points were measured on an Electrothermal 9100 apparatus and are uncorrected. Elemental analyses were performed using a Heraeus CHN-O-Rapid analyzer. DiscussionQuinoline derivatives are important heterocycles in bio-organic chemistry and are present in many natural products and pharmaceuticals [1]. In recent years there has been increasing interest in the determination of X-ray crystal structures of biologically active compounds [2][3][4][5][6][7][8].In the crystal structure of the title compound, the covalent bonds are found to be in normal range. Relevant bond lengths.486(4) Å and bond angles ÐC12-O3-C13 = 115.2(2)°, ÐC10-N1-C1 = 125.6(2)°, ÐN1-C7-C8 = 109.5(2)°, ÐC9-C8-C14 = 122.2 (2)°, ÐO1-C10-N1 = 120.1(2)°are almost similar to those in previous reports [2][3][4][5][6][7][8]. The methyl groups at O3 and O5 are approximately in the O3-C12-O2 (ÐC13-O3-C12-O2 = 4.1(4)°) and O5-C14-O4 (ÐC15-O5-C14-O4 = 2.1(4)°) planes, respectively, that agree well with a participation of O3 and O5 in electron donation to the carbonyl groups. The torsion angle ÐC9-C8-C14-O4 = -173.6(3)°shows clearly that the carbonyl group C14=O4 and the double bond C8=C9 share approximately a common plane with S-trans conformation, which probably is a result of the p-system conjugation. p-p-ring stacking is observed within the crystals probably as a result of the presence of parallel aromatic rings which stabilizes the crystal packing.

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“…Quinolines are interesting synthetic targets because they act as building blocks for a large number of natural products. Dialkyl 1,2-dihydroquinoline-2,3-dicarboxylates (97) are formed in a one-pot reaction from amide derivatives of 2-aminobenzaldehyde (95), DAAD (2) and TPP (1) in CH 2 Cl 2 in high yields (Scheme 29) [124,125].…”

Section: Reaction Of Triphenylphosphine Dialkyl Acetylenedicarboxylamentioning

confidence: 99%

Preparation of Stabilized Phosphorus Ylides via Multicomponent Reactions and Their Synthetic Applications

Ramazani

Kazemizadeh

2011

COC

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Triphenylphosphine (TPP), dialkyl acetylenedicarboxylates (DAAD), and acids such as phenols, imides, amides, enols, oximes and alcohols react with each other via a multicomponent reaction to produce stabilized phosphorus ylides. The reactions take place easily, through formation of intermediate formed by the Michael addition of the triphenylphosphine to dialkyl acetylenedicarboxylates and concomitant protonation of the intermediate by an acid leads to vinyltriphenylphosphonium salts. The salts are unstable intermediates and undergo a subsequent Michael addition leads to stabilized phosphorus ylides. In some cases ylide products are stable, but in other cases they cannot be isolated and appear to occur as intermediates on the pathway to an observed product. The stabilized phosphorus ylides are able to take part in the normal intramolecular Wittig reactions and produce a variety of heterocyclic or carbocyclic compounds, but they are not able to participate in the intermolecular Wittig reactions.

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One-step Synthesis of Dialkyl 1,2-Dihydroquinoline-2,3-dicarboxylates. A Vinyltriphenylphosphonium Salt Mediated Intramolecular Wittig Reaction†

Cited by 33 publications

References 11 publications

Augmented indoles

Augmented indoles

Crystal structure of dimethyl 1-acetyl-1,2-dihydro-2,3-quinolinedicarboxylate, C15H15NO5

Preparation of Stabilized Phosphorus Ylides via Multicomponent Reactions and Their Synthetic Applications

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