Some acid-catalysed reactions of indol-3-yl and indol-2-yl disubstituted methanols

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Title:Some acid-catalysed reactions of indol-3-yl and indol-2-yl disubstituted methanols
Creators:
Santoso, Mardi
Kumar, Naresh
Black, David StClair
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 74, 7-8, pp. 1137-1150
Uncontrolled Keywords:Acid-catalysed addition reactions, Indolocarbazoles, Isatins, Diindol-3-ylmethanes, Ketone reduction, Indoles

Abstract

1-Substituted indol-3-yl and indol-2-yl disubstituted methanols do not undergo acid-catalysed trimerisation to yield indolocyclotriveratrylenes, unlike the related primary 1-substituted indol-3-yl- and -2-ylmethanols. The 1-substituted indol-3-ylmethanols <b>10</b> and <b>11</b> gave diindol-3-ylmethanes <b>12</b> and <b>13</b>, respectively, on treatment with <i>p</i>-toluenesulfonic acid in dichloromethane. In contrast, the indol-2-ylmethanols <b>22</b> and <b>23</b> gave the reduced indolo[3,2-<i>b</i>]carbazoles <b>24</b> and <b>25</b>, respectively, on treatment with boron trifluoride etherate in benzene. An X-ray crystal structure of compound <b>24</b> is described.

Title:Some acid-catalysed reactions of indol-3-yl and indol-2-yl disubstituted methanols
Creators:
Santoso, Mardi
Kumar, Naresh
Black, David StClair
Uncontrolled Keywords:Acid-catalysed addition reactions, Indolocarbazoles, Isatins, Diindol-3-ylmethanes, Ketone reduction, Indoles
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:74
Number:7-8
Page Range:pp. 1137-1150
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc2009023UNSPECIFIED
ID Code:4526
Item Type:Article
Deposited On:01 Sep 2009 12:41
Last Modified:01 Sep 2009 10:41

Citation

Santoso, Mardi; Kumar, Naresh; Black, David StClair (2009) Some acid-catalysed reactions of indol-3-yl and indol-2-yl disubstituted methanols. Collection of Czechoslovak Chemical Communications, 74 (7-8). pp. 1137-1150. ISSN 0010-0765

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