1973
DOI: 10.1016/0040-4020(73)80047-x
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Synthesis and reactions of some 3-(2-haloacyl)indoles

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1973
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Cited by 63 publications
(44 citation statements)
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“…105 °C [13]) does not match that of the well-known compound 4 (mp. 233-234 °C [14], 230-232 °C [1]), but is quite close to that previously recorded for 1-(chloroacetyl)indole 3 (mp 116-117 °C [12], 115 °C [11], 120-121 °C [15]). The structure of 3 as a 1-substituted derivative of indole has also been rigorously proven a long time ago by dehydrogenation of 1-(chloroacetyl)-indole with DDQ [12].…”
Section: Resultssupporting
confidence: 85%
See 1 more Smart Citation
“…105 °C [13]) does not match that of the well-known compound 4 (mp. 233-234 °C [14], 230-232 °C [1]), but is quite close to that previously recorded for 1-(chloroacetyl)indole 3 (mp 116-117 °C [12], 115 °C [11], 120-121 °C [15]). The structure of 3 as a 1-substituted derivative of indole has also been rigorously proven a long time ago by dehydrogenation of 1-(chloroacetyl)-indole with DDQ [12].…”
Section: Resultssupporting
confidence: 85%
“…The common practical routes to 3-acylindoles and related compounds involve for instance treatment of indoles with acyl chlorides in the presence of pyridine [1], exposure of zincated indoles to acyl chlorides [2], Friedel-Crafts type acylation of indoles with acyl chlorides in the presence of Lewis acids [3,4], or Friedel-Crafts reactions of indoles possessing electron withdrawing N-substituents [5]. In addition, dimeric 3-acylindoles connected by long alkyl chains have been prepared by exposure of indole to bisimidazoline derivatives in acetic anhydride [6].…”
Section: Introductionmentioning
confidence: 99%
“…Analogues 2 a-d, retaining the carbonyl moiety adjacent to the indole 3-position, were prepared by reaction of indole with chloroacetyl chloride, [9] followed by displacement of chloride by each of a small set of amines (Scheme 1 a). Related compounds 3 a-d, retaining the alternative carbonyl group, were prepared by straightforward amide coupling reactions between indole-3-acetic acid and the same set of amines (Scheme 1 b).…”
Section: Modifications To the Glyoxylamide Substructurementioning
confidence: 99%
“…The 6-unsubstituted compound 15 was prepared as previously described 7 by acylation of indole with chloroacetyl chloride, 10 followed by halide exchange (Scheme 2). The N-Boc-6-bromo derivative 19 was prepared differently.…”
Section: Introductionmentioning
confidence: 99%