New Psychotropic Agents. Derivatives of Dibenzo[a,d]-1,4-cycloheptadiene

Winthrop, Stanley O.; Davis, Michael A.; Myers, Gordon S.; Gavin, J. G.; Thomas, R. A.; Barber, Randy B.

doi:10.1021/jo01048a057

Cited by 42 publications

(17 citation statements)

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“…Diol 84 was converted to suberene 86 by using a consecutive DMP oxidation and TiCl 4 -mediated McMurry reaction protocol. To our delight, we found compound 86 has significant utility in preparing miscellaneous medicinally important molecules [49][50][51] . For example, cyproheptadine 87, an antihistaminic and antiserotonergic agent, could be prepared by following reported procedures in three steps 52,53 .…”

Section: Resultsmentioning

confidence: 99%

Easy access to medium-sized lactones through metal carbene migratory insertion enabled 1,4-palladium shift

et al. 2020

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Reactions that efficiently construct medium-sized lactones are significant, as they overcome the unfavorable entropic factor and transannular interactions for ring closure, and the lactones produced are common structural motifs recurring in many biologically active compounds. Herein, we describe a valuable strategy for medium-sized lactone synthesis by accomplishing site-selective C-H bond functionalization via a palladium carbene migratory insertion enabled 1,4-palladium shift. The overall process achieves the formal dimerization of two readily available benzaldehyde derivatives, providing value-added products mediumsized lactones. Our method is amenable to late-stage modification of approved drugs and other complex molecules. Mechanistic studies including deuterium-labeling experiments and DFT calculation shed light on the reaction pathways.

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Section: Resultsmentioning

confidence: 99%

Easy access to medium-sized lactones through metal carbene migratory insertion enabled 1,4-palladium shift

et al. 2020

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“…In contrast, acid-catalyzed azeotropic water removal from 5-hydroxy-l0,ll -dihydro-5H-dibenzo [a,d]-cycloheptene gave little or no 5H-dibenzo[a,d]-cycloheptene.' It is also significant that numerous 5-hydroxy-5-alkyl-l0,ll-dihydrodibenzo [a,d]-cycloheptene derivatives are apparently converted exclusively to the 5-alkylidene compounds in a wide variety of acid-containing media (9).…”

Section: H-dibenzo [Ad]cycloheptene-5-carboxylicmentioning

confidence: 99%

“…Catalytic reduction of the unsaturated ketone (7) with 2 moles of deuterium (we were unable to selectively reduce the olefinic function) gave a mixture of which the alcohol (8) was the main constituent. The alcohol was not rigorously purified, but instead it was oxidized with manganese dioxide to deuterated dibenzosuberone (9) and this ketone was then converted to the hydroxy acid according to the published (6) procedure. The acid was esterified with excess diazomethane in methanol-ether solution.…”

Section: H-dibenzo [Ad]cycloheptene-5-carboxylicmentioning

confidence: 99%

Synthesis of 5H-dibenzo[a,d]cycloheptene-5-carboxylic acid and related compounds. 1,5-Hydride transfer to inductively destabilized carbonium ions

Horning¹,

Muchowski²

1968

Can. J. Chem.

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The synthesis of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carboxylic acid (2) and several derivatives of 5H-dibenzo[a,d]cycloheptene-5-carboxylic acid (1; a-c) from 5-hydroxy-l0,ll-dihydro-5H-dibenzo[a,d]cycloheptene-5-carboxylic acid and derivatives thereof (3; a-c) is described.The p-toluenesulfonic acid-catalyzed elimination of water (at 110.6" in toluene) from the deuterated hydroxy ester (3b; C-10, 11 d2) resulted in the incorporation of deuterium at C-5 of the olefinic ester l b with a KH/KD of 2.76. The large magnitude of this isotope effect indicated that the reaction proceeded via a rate-determining transannular 1,Shydride transfer from one of the benzylic positions of 36 t o the carbonium ion generated alpha to the methoxy-carbonyl group.

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“…Compound Vb 1701 Compound IIa [71] Compound 1B [72] ID 22 (SANDOZ) [73] Compound 20B (721 Scheme 14. Synthesis of 10.1 I-dihydrodibenzocycloheptenes with a C-C-C-N side chain.…”

Section: S a R O T E N E B (Lwdbeck)mentioning

confidence: 99%

Some new Developments in the Chemistry of Psychotherapeutic Agents

Jucker¹

1963

Angew. Chem. Int. Ed. Engl.

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New Psychotropic Agents. Derivatives of Dibenzo[a,d]-1,4-cycloheptadiene

Cited by 42 publications

References 0 publications

Easy access to medium-sized lactones through metal carbene migratory insertion enabled 1,4-palladium shift

Easy access to medium-sized lactones through metal carbene migratory insertion enabled 1,4-palladium shift

Synthesis of 5H-dibenzo[a,d]cycloheptene-5-carboxylic acid and related compounds. 1,5-Hydride transfer to inductively destabilized carbonium ions

Some new Developments in the Chemistry of Psychotherapeutic Agents

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