Reactions of 1,4-Diphenyl-1-bromo-3-butene-2-one. I. A Synthesis of 1-Aryl-2,5-diphenyl-3-pyrrolidones

Southwick, Philip L.; Sapper, David I.; Pursglove, L. A.

doi:10.1021/ja01167a028

Cited by 8 publications

(6 citation statements)

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“…chim. phys., [3 ] 46, 151 (1856); Wolkowa, Z. Chem., 579 (1870); or note the slow hydrolysis of saccharin, Suter, "Organic Chemistry of Sulfur," John Wiley and Sons, Inc., New York, N. Y., 1944, p. 623.…”

Section: Methodsmentioning

confidence: 99%

Purity Determination with the Electron Microscope

Lauffer¹

1951

J. Am. Chem. Soc.

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Section: Methodsmentioning

confidence: 99%

Purity Determination with the Electron Microscope

Lauffer¹

1951

J. Am. Chem. Soc.

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“…Cyclization of 45 in sodium methoxide followed by acid hydrolysis and decarboxylation gave 1-isopropyl-3-pyrrolidinone 46 (Scheme18) [19]. 46 …”

Section: Scheme 17mentioning

confidence: 99%

“…3-Substituted-3-hydroxypyrrolidines (R,R 1 = Me, Et; Z = OH, CHPh 2 ; OH, 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl, CPh 2 , 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene; 5,6,7,12-tetrahydrodibenzo[a,d]cycloocten-12-ylidene) 142 were prepared by reaction of 3-pyrrolidinones with a suitable hydrocarbon in the presence of BuLi followed by optional dehydration (Figure 12) [46]. Lithiation of 2-bromo-6-substituted naphthalene followed by stereoselective addition to 3-pyrrolidinone derivative 35 gave a racemic mixture of 3-naphthyl-3hydroxypyrrolidine hydrochloride 143 (R = H, F, OCH 3 ) (Scheme 54) [48].…”

Section: Scheme 52mentioning

confidence: 99%

“…The benzamide 201 acts as nervous system depressants [93], quinoline derivative 181 is useful as appetite depressants [79], and pyrrolidinyl naphthalene 143 has antinociceptive activity ( Figure 25) [48]. 3-Substituted-3-hydroxypyrrolidines 142 have parasympthomimetic activity [46]. 3-Hydroxy-3-(substituted alkyl)pyrrolidines 203 (Ar 1 =(subs.…”

Section: Medicinal Applicationsmentioning

confidence: 99%

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Synthesis and reactions of 3‐pyrrolidinones

Amer

Hammouda

Abdel‐Wahab

et al. 2008

Journal of Heterocyclic Chem

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N O R R 1 I This review presents a survey of the synthetic methods and reactions of 3-pyrrolidinones I (R = H, alkyl, acyl, ester; R 1 = H, alkyl, cyano, ester, etc). 3-Pyrrolidinones are synthetically versatiles substrate, as they can be used for synthesis of a large variety of heterocyclic compounds, such as indoles and 5-deazapteroic acid analogues and as a raw material for drug synthesis. The high reactivity of an active methylene group next to the carbonyl of the pyrrolidine ring is useful for various syntheses.

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“…La photolyse de pyrrolidines en prksence de benzophCnone, comme accepteur d'hydrogkne, conduit au pyrrole correspondant (29). Le 1,2,5-triphenylpyrrole a pu &tre obtenu par dCshydrogCnation de la pyrrolidine de depart, au reflux du p-cymkne, et en prCsence de chloranil (30). Nous proposons dans cette Ctude une nouvelle mCthode de synthkse de composCs pyrroliques, par oxydation avec du dioxyde de mangankse, sous irradiation micro-ondes.…”

Section: Introductionunclassified