Molecular iodine-mediated cascade reaction of 2-alkynylbenzaldehyde and indole: An easy access to tetracyclic indoloazulene derivatives

Sachin D. Gawande, Veerababurao Kavala, Manoj R. Zanwar, Chun Wei Kuo, Hsiu Ni Huang, Chiu Hui He, Ting Shen Kuo, Ching-Fa Yao

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The synthesis of iodo-substituted tetracyclic indole fused azulene derivatives was achieved from the reaction of 2-(substituted phenylethynyl)-benzaldehydes and different indoles in the presence of molecular iodine. The reaction involves the formation of a bisindole from the corresponding 2-(substituted phenylethynyl)benzaldehyde and indole followed by iodocyclization in a one-pot cascade process. A wide range of 2-(substituted phenylethynyl)-benzaldehydes and indoles were utilized in this protocol to derive a diverse range of iodo-substituted tetracyclic indole fused azulene derivatives in moderate to good yields. Further functionalizations of the iodo-substituted tetracyclic indole fused azulenes were achieved by various palladium-catalyzed crosscoupling reactions to generate highly substituted tetracyclic indole fused azulene derivatives.

Original languageEnglish
Pages (from-to)3022-3036
Number of pages15
JournalAdvanced Synthesis and Catalysis
Volume355
Issue number14-15
DOIs
Publication statusPublished - 2013 Jan 1

Fingerprint

Iodine
Derivatives
Benzaldehydes
Indoles
Azulenes
Palladium
indole
azulene

Keywords

  • Azulenes
  • Cascade process
  • Cross-coupling
  • Indoles
  • Indoloazulenes
  • Iodocyclization

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Molecular iodine-mediated cascade reaction of 2-alkynylbenzaldehyde and indole : An easy access to tetracyclic indoloazulene derivatives. / Gawande, Sachin D.; Kavala, Veerababurao; Zanwar, Manoj R.; Kuo, Chun Wei; Huang, Hsiu Ni; He, Chiu Hui; Kuo, Ting Shen; Yao, Ching-Fa.

In: Advanced Synthesis and Catalysis, Vol. 355, No. 14-15, 01.01.2013, p. 3022-3036.

Research output: Contribution to journalArticle

Gawande, Sachin D. ; Kavala, Veerababurao ; Zanwar, Manoj R. ; Kuo, Chun Wei ; Huang, Hsiu Ni ; He, Chiu Hui ; Kuo, Ting Shen ; Yao, Ching-Fa. / Molecular iodine-mediated cascade reaction of 2-alkynylbenzaldehyde and indole : An easy access to tetracyclic indoloazulene derivatives. In: Advanced Synthesis and Catalysis. 2013 ; Vol. 355, No. 14-15. pp. 3022-3036.
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AU - Zanwar, Manoj R.

AU - Kuo, Chun Wei

AU - Huang, Hsiu Ni

AU - He, Chiu Hui

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AB - The synthesis of iodo-substituted tetracyclic indole fused azulene derivatives was achieved from the reaction of 2-(substituted phenylethynyl)-benzaldehydes and different indoles in the presence of molecular iodine. The reaction involves the formation of a bisindole from the corresponding 2-(substituted phenylethynyl)benzaldehyde and indole followed by iodocyclization in a one-pot cascade process. A wide range of 2-(substituted phenylethynyl)-benzaldehydes and indoles were utilized in this protocol to derive a diverse range of iodo-substituted tetracyclic indole fused azulene derivatives in moderate to good yields. Further functionalizations of the iodo-substituted tetracyclic indole fused azulenes were achieved by various palladium-catalyzed crosscoupling reactions to generate highly substituted tetracyclic indole fused azulene derivatives.

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