Cyclizative Condensations. IV. 3,3′ Alkylidenebisindoles from Methyl Ketones and Their Conversion to Indolo[2,3-bjcarbazoles

Wayland E Noland, M. R. Venkiteswaran

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Abstract

Condensation of acetone with 5-methylindole and 5-benzyloxyindole in refluxing acetic acid gave the bisindoles Ie and If. Similarly, condensation of acetophenone with indole, 1-methylindole, and 2-methylindole gave the corresponding bisindoles Ih, Ii, and IXc. Condensation of acetone with indole or with the corresponding bisindole (Id) in refluxing maleic acid solution gave the indolo[2,3-b]carbazole IIf, while the corresponding condensation of acetone with the bisindole (Ie) from 5-methylindole gave the indolo [2,3-b] carbazole IIg. Condensation of acetone with 1-methylindole or with the corresponding bisindole (Ig) in ethanolic hydrochloric acid gave the indolo [2,3-b] carbazole IIh. Condensation of indole with acetophenone in ethanolic hydrochloric acid gave the polymer VI and what is believed to be the related cyclic dimer, the indolo [3,2-b] carbazole VII, as indicated by its alternate method of synthesis from 3-( X-phenylvinyl)indole (IV) in ethanolic hydrochloric acid. Condensation of 1-methylindole with acetophenone in ethanolic hydrochloric acid gave only the bisindole Ii, Factors influencing formation of the various types of products described in this and preceding papers of the series are discussed and summarized.

Original languageEnglish (US)
Pages (from-to)4263-4269
Number of pages7
JournalJournal of Organic Chemistry
Volume26
Issue number11
DOIs
StatePublished - Nov 1961

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Ketones
Condensation
Hydrochloric Acid
Acetone
Acetic Acid
Dimers
Polymers
indole
indolo(3,2-b)carbazole
1-methylindole
acetophenone

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Cyclizative Condensations. IV. 3,3′ Alkylidenebisindoles from Methyl Ketones and Their Conversion to Indolo[2,3-bjcarbazoles. / Noland, Wayland E; Venkiteswaran, M. R.

In: Journal of Organic Chemistry, Vol. 26, No. 11, 11.1961, p. 4263-4269.

Research output: Contribution to journalArticle

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abstract = "Condensation of acetone with 5-methylindole and 5-benzyloxyindole in refluxing acetic acid gave the bisindoles Ie and If. Similarly, condensation of acetophenone with indole, 1-methylindole, and 2-methylindole gave the corresponding bisindoles Ih, Ii, and IXc. Condensation of acetone with indole or with the corresponding bisindole (Id) in refluxing maleic acid solution gave the indolo[2,3-b]carbazole IIf, while the corresponding condensation of acetone with the bisindole (Ie) from 5-methylindole gave the indolo [2,3-b] carbazole IIg. Condensation of acetone with 1-methylindole or with the corresponding bisindole (Ig) in ethanolic hydrochloric acid gave the indolo [2,3-b] carbazole IIh. Condensation of indole with acetophenone in ethanolic hydrochloric acid gave the polymer VI and what is believed to be the related cyclic dimer, the indolo [3,2-b] carbazole VII, as indicated by its alternate method of synthesis from 3-( X-phenylvinyl)indole (IV) in ethanolic hydrochloric acid. Condensation of 1-methylindole with acetophenone in ethanolic hydrochloric acid gave only the bisindole Ii, Factors influencing formation of the various types of products described in this and preceding papers of the series are discussed and summarized.",
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AB - Condensation of acetone with 5-methylindole and 5-benzyloxyindole in refluxing acetic acid gave the bisindoles Ie and If. Similarly, condensation of acetophenone with indole, 1-methylindole, and 2-methylindole gave the corresponding bisindoles Ih, Ii, and IXc. Condensation of acetone with indole or with the corresponding bisindole (Id) in refluxing maleic acid solution gave the indolo[2,3-b]carbazole IIf, while the corresponding condensation of acetone with the bisindole (Ie) from 5-methylindole gave the indolo [2,3-b] carbazole IIg. Condensation of acetone with 1-methylindole or with the corresponding bisindole (Ig) in ethanolic hydrochloric acid gave the indolo [2,3-b] carbazole IIh. Condensation of indole with acetophenone in ethanolic hydrochloric acid gave the polymer VI and what is believed to be the related cyclic dimer, the indolo [3,2-b] carbazole VII, as indicated by its alternate method of synthesis from 3-( X-phenylvinyl)indole (IV) in ethanolic hydrochloric acid. Condensation of 1-methylindole with acetophenone in ethanolic hydrochloric acid gave only the bisindole Ii, Factors influencing formation of the various types of products described in this and preceding papers of the series are discussed and summarized.

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