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

doi:10.1016/j.tetlet.2018.11.037

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^*

^*Corresponding author for this work

Department of Pharmaceutical Biotechnology, Manipal College of Pharmaceutical Sciences, Manipal
Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal

Research output: Contribution to journal › Article › peer-review

12 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 language	English
Pages (from-to)	4587-4592
Number of pages	6
Journal	Tetrahedron Letters
Volume	59
Issue number	52
DOIs	https://doi.org/10.1016/j.tetlet.2018.11.037
Publication status	Published - 26-12-2018

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2018.11.037

Cite this

Sujeevan Reddy, G., Babu Nallapati, S., Sri Saranya, P. S. V. K., Sridhar, B., Bhat Giliyaru, V., Chandrashekhar Hariharapura, R., Gautham Shenoy, G., & Pal, M. (2018). Propargylamine (secondary) as a building block in indole synthesis involving ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method: Unexpected formation of (pyrazole)imine derivatives. Tetrahedron Letters, 59(52), 4587-4592. https://doi.org/10.1016/j.tetlet.2018.11.037

@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",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = dec,

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 Ltd",

number = "52",

}

Sujeevan Reddy, G, Babu Nallapati, S, Sri Saranya, PSVK, Sridhar, B, Bhat Giliyaru, V, Chandrashekhar Hariharapura, R , Gautham Shenoy, G & Pal, M 2018, 'Propargylamine (secondary) as a building block in indole synthesis involving ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method: Unexpected formation of (pyrazole)imine derivatives', Tetrahedron Letters, vol. 59, no. 52, pp. 4587-4592. https://doi.org/10.1016/j.tetlet.2018.11.037

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

Research output: Contribution to journal › Article › peer-review

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 - https://www.scopus.com/pages/publications/85056997461

UR - https://www.scopus.com/pages/publications/85056997461#tab=citedBy

U2 - 10.1016/j.tetlet.2018.11.037

DO - 10.1016/j.tetlet.2018.11.037

M3 - Article

AN - SCOPUS:85056997461

SN - 0040-4039

VL - 59

SP - 4587

EP - 4592

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 52

ER -

Sujeevan Reddy G, Babu Nallapati S, Sri Saranya PSVK, Sridhar B, Bhat Giliyaru V, Chandrashekhar Hariharapura R et al. Propargylamine (secondary) as a building block in indole synthesis involving ultrasound assisted Pd/Cu-catalyzed coupling-cyclization method: Unexpected formation of (pyrazole)imine derivatives. Tetrahedron Letters. 2018 Dec 26;59(52):4587-4592. doi: 10.1016/j.tetlet.2018.11.037

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

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this