Propargylamine (secondary) as a building block in indole synthesis involving ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method: Unexpected formation of (pyrazole)imine derivatives

Gangireddy Sujeevan Reddy, Suresh Babu Nallapati, P. S.V.K. Sri Saranya, B. Sridhar, Varadaraj Bhat Giliyaru, Raghu Chandrashekhar Hariharapura, G. Gautham Shenoy, Manojit Pal

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Propargylamine (secondary) has been explored as a building block in synthesizing indoles via an ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method. Indoles containing a pyrazole moiety at C-2 attached via the –CH2NH– linker (designed as potential anti-tubercular agents) were synthesized first and then generality/scope of the methodology was expanded by synthesizing other indoles. Unexpected formation of imine side products in first cases helped in synthesizing related (pyrazole)imines via a Cu catalyzed ultrasound assisted aerobic oxidation of precursor amines.

Original languageEnglish
Pages (from-to)4587-4592
Number of pages6
JournalTetrahedron Letters
Volume59
Issue number52
DOIs
Publication statusPublished - 26-12-2018

Fingerprint

Indoles
Imines
Cyclization
Ultrasonics
Derivatives
Amines
Oxidation
propargylamine
indole
pyrazole

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Sujeevan Reddy, Gangireddy ; Babu Nallapati, Suresh ; Sri Saranya, P. S.V.K. ; Sridhar, B. ; Bhat Giliyaru, Varadaraj ; Chandrashekhar Hariharapura, Raghu ; Gautham Shenoy, G. ; Pal, Manojit. / Propargylamine (secondary) as a building block in indole synthesis involving ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method : Unexpected formation of (pyrazole)imine derivatives. In: Tetrahedron Letters. 2018 ; Vol. 59, No. 52. pp. 4587-4592.
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Propargylamine (secondary) as a building block in indole synthesis involving ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method : Unexpected formation of (pyrazole)imine derivatives. / Sujeevan Reddy, Gangireddy; Babu Nallapati, Suresh; Sri Saranya, P. S.V.K.; Sridhar, B.; Bhat Giliyaru, Varadaraj; Chandrashekhar Hariharapura, Raghu; Gautham Shenoy, G.; Pal, Manojit.

In: Tetrahedron Letters, Vol. 59, No. 52, 26.12.2018, p. 4587-4592.

Research output: Contribution to journalArticle

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AU - Sujeevan Reddy, Gangireddy

AU - Babu Nallapati, Suresh

AU - Sri Saranya, P. S.V.K.

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AU - Gautham Shenoy, G.

AU - Pal, Manojit

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