Preparation of vinylogous 2-sulfonylindolines by the palladium-catalyzed cyclization of 1-sulfonyl-1,3-dienes with N-Cbz-o-Iodoanilines

Back, Thomas G.; Bethell, Richard J.

doi:10.1016/s0040-4039(98)01111-3

Cited by 25 publications

(6 citation statements)

References 13 publications

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“…380,381 Allenes in this Pd-catalyzed indole synthesis variation lead to 7-azaindolinones following ozonolysis of the initially formed exo-methyleneindoline, 382 and 1-sulfonyl-1,3-dienes in the Larock methodology lead to 2-vinylindolines. 383 1-Oxygenated dienes also work well. 384…”

Section: Larock Indole Synthesismentioning

confidence: 97%

Recent developments in indole ring synthesis—methodology and applications

Gribble

2000

J. Chem. Soc., Perkin Trans. 1

965

294

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Section: Larock Indole Synthesismentioning

confidence: 97%

Recent developments in indole ring synthesis—methodology and applications

Gribble

2000

J. Chem. Soc., Perkin Trans. 1

965

294

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“…We now report that the palladium-catalyzed reactions of variously p -substituted o -iodoanilines 1 with dienyl sulfones 2 afford vinylogous 2-sulfonylindolines 3 . We also report that the products 3 undergo facile oxidation with DDQ to the corresponding indoles 4 , which in turn can be employed as dienes in highly regioselective Diels−Alder cycloaddditions that lead, after desulfonylation, to carbazoles containing substituents at the 3-, 4-, and/or 6-positions (Scheme ).…”

mentioning

confidence: 82%

Preparation of Vinylogous 2-Sulfonylindolines by the Palladium-Catalyzed Heteroannulation of o-Iodoanilines with Dienyl Sulfones and Their Further Transformation to Indoles and Carbazoles

et al. 2001

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The palladium-catalyzed heteroannulation of o-iodoanilines with dienyl sulfones provides a convenient route to vinylogous 2-sulfonylindolines 3. The reaction proceeds in DMF/water in the presence of potassium carbonate and catalytic palladium(II) acetate and is compatible with both electron-donating and -withdrawing substituents in the para position of the aniline, and with an alkyl substituent at C-2 of the dienyl sulfone. The indolines underwent oxidation with DDQ to afford the corresponding indoles 4. The latter were then employed as dienes in Diels-Alder reactions with dimethyl acetylenedicarboxylate (DMAD), methyl propiolate, or methyl acrylate. In the case of the latter two dienophiles, the cycloadditions were highly regioselective, affording the corresponding 1,3-products (with respect to the relative positions of the sulfone and ester groups), exclusively. The cycloadducts from acetylenic dienophiles were converted to the corresponding carbazoles by elimination of the sulfone moiety with DBU, and that from methyl acrylate was subjected to reductive desulfonylation and oxidation to the corresponding carbazole with DDQ. The method thus provides access to carbazoles with various substituents at the 3-, 4-, and 6-positions.

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“…One pot Suzuki coupling of 1,1-dibromo-1-alkenes (35) with p-methoxyphenylboronic acid (36) under conditions of palladium catalysis to get 2-substituted indoles (37) was described by Bisseret and co-workers [54]. Convergent synthesis of psilocin (41) [55] from N-tertbutoxycarbonyl-2-iodo-3-methoxyaniline (38) with various Utimato's approach to the preparation of 3-allylindoles via palladium catalysis was used by Cacchi et al [45][46][47][48] Back et al [56,57] reported that the palladium catalyzed reactions of various p-substituted o-iodoanilines (42) with dienyl sulfones afforded vinylogous 2-sulfonylindolines, were oxidized by DDQ to give the corresponding indoles (44). The indoles (44) in turn can be employed as dienes in highly regioselective Diels-Alder cycloadditions that lead after desulfonilation to carbazoles (45) containing substituents at the 3,4 and/or 6 positions.…”

Section: Heteroannulation (Heck Reaction)mentioning

confidence: 99%

Recent Uses of Palladium Chemistry in Indole Synthesis

Buolamwini¹

2006

COS

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Preparation of vinylogous 2-sulfonylindolines by the palladium-catalyzed cyclization of 1-sulfonyl-1,3-dienes with N-Cbz-o-Iodoanilines

Cited by 25 publications

References 13 publications

Recent developments in indole ring synthesis—methodology and applications

Recent developments in indole ring synthesis—methodology and applications

Preparation of Vinylogous 2-Sulfonylindolines by the Palladium-Catalyzed Heteroannulation of o-Iodoanilines with Dienyl Sulfones and Their Further Transformation to Indoles and Carbazoles

Recent Uses of Palladium Chemistry in Indole Synthesis

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