Alkylation of 3-Ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydroindole with Bromoesters: Benzenesulfonyl as Convenient Nitrogen Protecting Group

Masaguer, Christian F.; Raviña, Enrique; Fueyo, J.

doi:10.3987/com-91-5889

Cited by 14 publications

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“…In search of analogs of the well-established antipsychotics Molindone and Piquindone, N -benzenesulfonyl-protected 4,5,6,7-tetrahydroindol-4-one 204 was alkylated with α -bromoesters 205 with lithium diisopropylamide (LDA) as a base ( Scheme 37 ) [ 100 ]. One-pot benzenesulfonyl deprotection and ester hydrolysis of 206 afforded potential antipsychotics 207 with only one diastereomer (if R = Me) isolated.…”

Section: Synthesis Of [45]-fused Polyheterocyclic Structuresmentioning

confidence: 99%

4,5,6,7-Tetrahydroindol-4-Ones as a Valuable Starting Point for the Synthesis of Polyheterocyclic Structures

Horsten¹,

Dehaen²

2021

Molecules

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This review focuses on the synthesis of polyheterocyclic structures with a variety of medicinal and optoelectronic applications, starting from readily available 4,5,6,7-tetrahydroindol-4-one analogs. First, routes toward the 4,5,6,7-tetrahydroindol-4-one starting materials are summarized, followed by synthetic pathways towards polyheterocyclic structures which are categorized based on the size and attachment point of the newly formed (hetero)cyclic ring.

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Section: Synthesis Of [45]-fused Polyheterocyclic Structuresmentioning

confidence: 99%

4,5,6,7-Tetrahydroindol-4-Ones as a Valuable Starting Point for the Synthesis of Polyheterocyclic Structures

Horsten¹,

Dehaen²

2021

Molecules

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Protection for the Amino Group

Wuts

Greene²

2006

Greene's Protective Groups in Organic Synthesis

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Protection for the Amino Group

2014

Greene's Protective Groups in Organic Synthesis

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CARBAMATES 907Carbamate Derived from an Amine and CO 2 , 908 Methyl and Ethyl, 909 9-Fluorenylmethyl, 912 2,6-Di-t-butyl-9-fluorenylmethyl, 915 2,7-Bis (trimethylsilyl)fluorenylmethyl, 915 2-(2-Ethylhexyl)-9-fluorenylmethyl, 915 2,7-Bis-(2-ethylhexyl)-9-fluorenylmethyl, 915 9-(2-Sulfo)fluorenylmethyl, 916 9-(2,7-Dibromo)fluorenylmethyl, 916 17-Tetrabenzo[a,c,g,i]fluorenylmethyl, 916 2-Chloro-3-indenylmethyl, 916 Benz[f]inden-3-ylmethyl, 916 1,1-Dioxobenzo[b]thiophene-2-ylmethyl, 917 2,7-Di-t-butyl[9-(10,10-dioxo-10,10,10,10-tetrahydrothioxanthyl)]methyl, 917 Azidomethyl, 920 2-(Hydroxymethyl)-3-phenyl-4H-1-benzothiopyran-4-one 1,1-Dioxide, 920 2-Methylsulfonyl-3-phenyl-1-prop-2-enyloxy, 920 Substituted Ethyl Carbamates 921 2,2,2-Trichloroethyl, 921 2-Trimethylsilylethyl, 923 (2-Phenyl-2-trimethylsilyl)ethyl, 925 2-(Triphenylsilyl)ethyl, 925 2-Phenylethyl, 927 2-Chloroethyl, 927 2 3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-decyl, 927 1,1-Dimethyl-2-haloethyl, 927 1,1-Dimethyl-2,2-dibromoethyl, 927 1,1-Dimethyl-2,2,2-trichloroethyl, 928 2-(2´and 4´-Pyridyl)ethyl, 928

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Alkylation of 3-Ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydroindole with Bromoesters: Benzenesulfonyl as Convenient Nitrogen Protecting Group

Cited by 14 publications

References 0 publications

4,5,6,7-Tetrahydroindol-4-Ones as a Valuable Starting Point for the Synthesis of Polyheterocyclic Structures

4,5,6,7-Tetrahydroindol-4-Ones as a Valuable Starting Point for the Synthesis of Polyheterocyclic Structures

Protection for the Amino Group

Protection for the Amino Group

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