Ortho-lithiation of aryloxazolines

Gschwend, Heinz W.; Hamdan, Ali

doi:10.1021/jo00901a036

Cited by 127 publications

(61 citation statements)

References 4 publications

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“…After aqueous quenching, the product was extracted with diethyl ether ( Anal. Calcd for C19H,,N0,: C , H,7.18;N,77.00;H,[7][8][9][10][11][12][13][14][15][16][17][18]N,4.75. …”

Section: Chemicals and Solventsmentioning

confidence: 99%

Anionic Synthesis of Aromatic Carboxyl Functionalized Polymers. Chain-End Functionalization of Poly(styryl)lithium with 4,5-Dihydro-4,4-dimethyl-2- [4-(1-phenylethenyl)phenyl]oxazole

Summers

Quirk

1996

Polym. Int.

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“…After aqueous quenching, the product was extracted with diethyl ether ( Anal. Calcd for C19H,,N0,: C , H,7.18;N,77.00;H,[7][8][9][10][11][12][13][14][15][16][17][18]N,4.75. …”

Section: Chemicals and Solventsmentioning

confidence: 99%

Anionic Synthesis of Aromatic Carboxyl Functionalized Polymers. Chain-End Functionalization of Poly(styryl)lithium with 4,5-Dihydro-4,4-dimethyl-2- [4-(1-phenylethenyl)phenyl]oxazole

Summers

Quirk

1996

Polym. Int.

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“…The oxazoline 8 was lithiated with n-BuLi (22,23) and treated with an excess of ethylene oxide to give compound 13 which was hydrolysed (24) 2-Methyl-3,4-dihydro-6,7-dimethoxy-8-(3,4-dimethoxypheny1)-l(2H)isoquinolinone 18 was prepared in an analogous series of reactions by the sequence 14 -+ 17 -+ 18.…”

Section: -mentioning

confidence: 99%

“…T w o key steps in this synthesis involve oxazoline chemistry, the first, directed displacement of the methoxy group ortho to the oxazoline by the method of Meyers and Mihelich (13), and the second, ortho lithiation of the oxazoline followed by alkylation with ethylene oxide (10,22,23).…”

Section: -mentioning

confidence: 99%

Synthesis of indeno[1,2,3-ĳ]isoquinolines

Patel¹,

MacLean²

1983

Can. J. Chem.

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1-Methyl and 1-benzyl-1,2,3,10b-tetrahydro-5,6,8,9-tetramethoxyindeno[1,2,3-ĳ]isoquinoline have been synthesized from the corresponding 8-phenyl-3,4-dihydro-1(2H)isoquinolinones by treatment with POCl3 under Vilsmeier conditions followed by borohydride reduction. The isoquinolinones were prepared in six steps from 2-(2,3,4-trimethoxyphenyl)-4,4-dimethyl-2-oxazoline. This sequence of reactions provides a new route to dihydro and tetrahydroindeno[1,2,3-ĳ]isoquinolines.

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“…Oxazolines have found utility as protecting groups in carboxylic acid chemistry [1], as a directing group in ortho-metallation reactions [2], as chiral auxiliaries in asymmetric synthesis [3] and as ligands in transition metal and main group coordination chemistry [4]. The oxazoline ring is also found in a number of (bioactive) natural products [5] and synthetic drugs [6].…”

Section: Introductionmentioning

confidence: 99%

Oxazoline chemistry part III. Synthesis and characterisation of [2‐(2′‐anilinyl)‐2‐oxazolines] and some related compounds

Button¹,

Gossage²

2003

Journal of Heterocyclic Chem

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The syntheses and characterisation of a series of chiral and achiral 2‐(aminophenyl)‐2‐oxazolines and some related compounds is reported. All of the derivatives have been produced by a one‐step procedure involving the treatment of isatoic anhydride (i.e. [2H]‐3, 1‐benzoxazine‐[1H‐2,4‐dione: 1) or its 5‐chloro analogue with a slight excess of appropriate amino‐alcohols. In most cases, anhydrous ZnCl2 is shown to be an effective Lewis acid catalyst for this reaction at reflux temperature in high boiling aromatic solvents (PhCl or PhMe). Oxazolines have been readily formed using rac‐2‐amino‐1‐butanol, (S)‐phenylglycinol, 2‐methyl‐2‐amino‐1‐propanol and (1S,2R) or (IR,2S)‐cis‐1‐amino‐2‐indanol; yields range from 85% to 22%. The use of aminoalcohols such as 2‐ethanolamine, (±)‐2‐amino‐1‐phenyl‐1‐propanol or 3‐amino‐1‐propanol (to give the corresponding 4,5‐dihydro‐1,3‐oxazine) results in poor yields. The use of other Lewis acid catalysts (silicic acid, Cd(acac)2·2H2O, CuCl2·2H2O, InCl3) or higher temperatures did not improve the yields with these latter two substrates. Benzoxazoles and N‐substituted benzoxazoles can also be obtained in reasonable yields from 1 using 2‐aminophenol (36%) or 2‐amino‐3‐hydroxypyridine (45%).

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Ortho-lithiation of aryloxazolines

Cited by 127 publications

References 4 publications

Anionic Synthesis of Aromatic Carboxyl Functionalized Polymers. Chain-End Functionalization of Poly(styryl)lithium with 4,5-Dihydro-4,4-dimethyl-2- [4-(1-phenylethenyl)phenyl]oxazole

Anionic Synthesis of Aromatic Carboxyl Functionalized Polymers. Chain-End Functionalization of Poly(styryl)lithium with 4,5-Dihydro-4,4-dimethyl-2- [4-(1-phenylethenyl)phenyl]oxazole

Synthesis of indeno[1,2,3-ĳ]isoquinolines

Oxazoline chemistry part III. Synthesis and characterisation of [2‐(2′‐anilinyl)‐2‐oxazolines] and some related compounds

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