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

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

7 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

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10.1016/j.tetlet.2018.11.037

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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

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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.",

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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

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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

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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.

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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

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