Synthesis of dl-deethylibogamine

Augustine, Robert L.; Pierson, William G.

doi:10.1021/jo01256a065

Cited by 18 publications

(4 citation statements)

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“…Synthesis of Tetrahydrobenzazepines. Compounds 1 , , 2 , 3 , 8 , and 11 , have been reported in the literature. For this study, most of these compounds were prepared from the corresponding tetralones either via a Beckmann rearrangement of their oximes or via a Schmidt rearrangement followed by LAH reduction and acylation.…”

Section: Methodsmentioning

confidence: 99%

Dynamic and Static Conformational Analysis of Acylated Tetrahydrobenzazepines

et al. 2003

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A detailed high-field NMR analysis of several acylated tetrahydrobenzazepines, supported by molecular mechanics calculations, indicates that the heterocyclic ring in these compounds exists in a chair conformation, with the carbonyl oriented anti to the aryl moiety in the dominant rotamer. Surprisingly, ring methylenes are typically diastereotopic at room temperature, as the barriers for the process of enantiomerization of the seven-membered ring are much higher than expected. It is shown that ring inversion is correlated (but not concerted) with rotation of the amide moiety, as the carbonyl is forced out of conjugation with the nitrogen in the transition state.

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Section: Methodsmentioning

confidence: 99%

Dynamic and Static Conformational Analysis of Acylated Tetrahydrobenzazepines

et al. 2003

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“…The title compounds were prepared starting from α-tetralone (7), which was reacted with hydrazoic acid to yield 1-benzazepine-2-one 8 by means of a Schmidt reaction [ 20 ]. Subsequent Friedel-Crafts acylation with acetyl chloride in carbon disulfide led to the acetophenone derivative 9 [ 21 ]. The enaminone 10 was then prepared from 9 by prolonged heating with dimethylformamide dimethyl acetal [ 22 ].…”

Section: Resultsmentioning

confidence: 99%

“… Anilinopyrimidines 2a – n . Reagents and conditions: (i) NaN 3 , H 2 SO 4 , AcOH, rt → 60 °C, 30 min, 67% [ 20 ]; (ii) AcCl, AlCl 3 , CS 2 , reflux, 1 h, then rt, 3 h, 67% [ 21 ]; (iii) DMF-DMA, 110–115 °C, 13 h, 59% [ 22 ]; (iv) propan-2-ol, NaOH, reflux, 15–30 h, (v) propan-2-ol, NaOH, microwave irradiation: 150 W, 140 °C, 30–90 min or (vi) DMF, NaOH, microwave irradiation: 150 W, 175 °C, 30–90 min. For substituents R refer to Table 3.…”

Section: Figures Schemes and Tablesmentioning

confidence: 99%

7-(2-Anilinopyrimidin-4-yl)-1-benzazepin-2-ones Designed by a “Cut and Glue” Strategy Are Dual Aurora A/VEGF-R Kinase Inhibitors

et al. 2021

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Although overexpression and hyperactivity of protein kinases are causative for a wide range of human cancers, protein kinase inhibitors currently approved as cancer drugs address only a limited number of these enzymes. To identify new chemotypes addressing alternative protein kinases, the basic structure of a known PLK1/VEGF-R2 inhibitor class was formally dissected and reassembled. The resulting 7-(2-anilinopyrimidin-4-yl)-1-benzazepin-2-ones were synthesized and proved to be dual inhibitors of Aurora A kinase and VEGF receptor kinases. Crystal structures of two representatives of the new chemotype in complex with Aurora A showed the ligand orientation in the ATP binding pocket and provided the basis for rational structural modifications. Congeners with attached sulfamide substituents retained Aurora A inhibitory activity. In vitro screening of two members of the new kinase inhibitor family against the cancer cell line panel of the National Cancer Institute (NCI) showed antiproliferative activity in the single-digit micromolar concentration range in the majority of the cell lines.

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“…Preparation of the Decalone 7.•-A mixture of the octalones 9, bp 115-132°( 0.08-0.1 mm), n28•5d 1.5073 [lit.7 bp 110-115°( 0.05 (6) All melting points are corrected and all boiling points are uncorrected. Unless otherwise stated, magnesium sulfate was employed as a drying agent.…”

Section: Experimental Section9mentioning

confidence: 99%

Chemistry of carbanions. XXI. Stereochemistry of enolate alkylation in the 1-decalone system

House¹,

Umen²

1972

J. Org. Chem.

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Reaction of the lithium 1''-enolate of syn-6-íert-butyl-írons-l-decalone (7) with methyl iodide yielded the same proportion of cis (13, 80-86%) and trans (14, 14-20%) monoalkylated products as was found in the analogous reaction with the 1-decalone enolate la. This result indicates that it is not necessary to postulate a transition state such as 4c to account for the predominant formation of 9-alkyl-as-l-decalones in alkylation reactions.The bridgehead alkylation of enolate anions 1 derived from either 1-decalone or perhydro-l-indanone produces predominantly the cis-fused product 2 (Scheme I) ;2 for example, the monoalkylated product Scheme I 5

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Synthesis of dl-deethylibogamine

Cited by 18 publications

References 1 publication

Dynamic and Static Conformational Analysis of Acylated Tetrahydrobenzazepines

Dynamic and Static Conformational Analysis of Acylated Tetrahydrobenzazepines

7-(2-Anilinopyrimidin-4-yl)-1-benzazepin-2-ones Designed by a “Cut and Glue” Strategy Are Dual Aurora A/VEGF-R Kinase Inhibitors

Chemistry of carbanions. XXI. Stereochemistry of enolate alkylation in the 1-decalone system

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