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

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.
@article{c255d7b893fd4b71b9a10c068b5bf924,
title = "Propargylamine (secondary) as a building block in indole synthesis involving ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method: Unexpected formation of (pyrazole)imine derivatives",
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.",
author = "{Sujeevan Reddy}, Gangireddy and {Babu Nallapati}, Suresh and {Sri Saranya}, {P. S.V.K.} and B. Sridhar and {Bhat Giliyaru}, Varadaraj and {Chandrashekhar Hariharapura}, Raghu and {Gautham Shenoy}, G. and Manojit Pal",
year = "2018",
month = "12",
day = "26",
doi = "10.1016/j.tetlet.2018.11.037",
language = "English",
volume = "59",
pages = "4587--4592",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "52",

}

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

TY - JOUR

T1 - Propargylamine (secondary) as a building block in indole synthesis involving ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method

T2 - Unexpected formation of (pyrazole)imine derivatives

AU - Sujeevan Reddy, Gangireddy

AU - Babu Nallapati, Suresh

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

AU - Sridhar, B.

AU - Bhat Giliyaru, Varadaraj

AU - Chandrashekhar Hariharapura, Raghu

AU - Gautham Shenoy, G.

AU - Pal, Manojit

PY - 2018/12/26

Y1 - 2018/12/26

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85056997461&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85056997461&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2018.11.037

DO - 10.1016/j.tetlet.2018.11.037

M3 - Article

VL - 59

SP - 4587

EP - 4592

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 52

ER -