K2CO3-Catalyzed Synthesis of 2,5-Dialkyl-4,6,7-tricyano-Decorated Indoles via Carbon-Carbon Bond Cleavage

Ryan A.S. Pike; Rishi R. Sapkota; Bijay Shrestha; Roshan K. Dhungana; Shekhar Kc; Diane A. Dickie; Ramesh Giri

doi:10.1021/acs.orglett.0c01057

K₂CO₃-Catalyzed Synthesis of 2,5-Dialkyl-4,6,7-tricyano-Decorated Indoles via Carbon-Carbon Bond Cleavage

Ryan A.S. Pike, Rishi R. Sapkota, Bijay Shrestha, Roshan K. Dhungana, Shekhar Kc, Diane A. Dickie, Ramesh Giri

Chemistry

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

10 Scopus citations

Abstract

We describe a novel method to synthesize 2,5-dialkyl-4,6,7-tricyanoindole derivatives from a base-catalyzed reaction of 1,3-diketones with fumaronitrile. The reaction proceeds by the condensation of two molecules of fumaronitrile and one molecule of 1,3-diketone in a remarkable process that involves the cleavage of one C(sp³)-C(sp²) bond in 1,3-diketones and the formation of one carbon-nitrogen bond and four carbon-carbon bonds to construct both the aryl and pyrrole rings of the indole in one step.

Original language	English (US)
Pages (from-to)	3268-3272
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.0c01057
State	Published - Apr 17 2020

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.0c01057

Cite this

@article{4b2ca7d8688b4057833c3b3fdb85cd93,

title = "K2CO3-Catalyzed Synthesis of 2,5-Dialkyl-4,6,7-tricyano-Decorated Indoles via Carbon-Carbon Bond Cleavage",

abstract = "We describe a novel method to synthesize 2,5-dialkyl-4,6,7-tricyanoindole derivatives from a base-catalyzed reaction of 1,3-diketones with fumaronitrile. The reaction proceeds by the condensation of two molecules of fumaronitrile and one molecule of 1,3-diketone in a remarkable process that involves the cleavage of one C(sp3)-C(sp2) bond in 1,3-diketones and the formation of one carbon-nitrogen bond and four carbon-carbon bonds to construct both the aryl and pyrrole rings of the indole in one step.",

author = "Pike, {Ryan A.S.} and Sapkota, {Rishi R.} and Bijay Shrestha and Dhungana, {Roshan K.} and Shekhar Kc and Dickie, {Diane A.} and Ramesh Giri",

note = "Funding Information: We gratefully acknowledge the NSF (no. CHE-1554299) for the support of this work. We also thank The Pennsylvania State University and the University of New Mexico (UNM) for additional financial support. R.A.S.P. also acknowledges the financial support from Industrial Water Engineering. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = apr,

day = "17",

doi = "10.1021/acs.orglett.0c01057",

language = "English (US)",

volume = "22",

pages = "3268--3272",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - K2CO3-Catalyzed Synthesis of 2,5-Dialkyl-4,6,7-tricyano-Decorated Indoles via Carbon-Carbon Bond Cleavage

AU - Pike, Ryan A.S.

AU - Sapkota, Rishi R.

AU - Shrestha, Bijay

AU - Dhungana, Roshan K.

AU - Kc, Shekhar

AU - Dickie, Diane A.

AU - Giri, Ramesh

N1 - Funding Information: We gratefully acknowledge the NSF (no. CHE-1554299) for the support of this work. We also thank The Pennsylvania State University and the University of New Mexico (UNM) for additional financial support. R.A.S.P. also acknowledges the financial support from Industrial Water Engineering. Publisher Copyright: Copyright © 2020 American Chemical Society.

PY - 2020/4/17

Y1 - 2020/4/17

N2 - We describe a novel method to synthesize 2,5-dialkyl-4,6,7-tricyanoindole derivatives from a base-catalyzed reaction of 1,3-diketones with fumaronitrile. The reaction proceeds by the condensation of two molecules of fumaronitrile and one molecule of 1,3-diketone in a remarkable process that involves the cleavage of one C(sp3)-C(sp2) bond in 1,3-diketones and the formation of one carbon-nitrogen bond and four carbon-carbon bonds to construct both the aryl and pyrrole rings of the indole in one step.

AB - We describe a novel method to synthesize 2,5-dialkyl-4,6,7-tricyanoindole derivatives from a base-catalyzed reaction of 1,3-diketones with fumaronitrile. The reaction proceeds by the condensation of two molecules of fumaronitrile and one molecule of 1,3-diketone in a remarkable process that involves the cleavage of one C(sp3)-C(sp2) bond in 1,3-diketones and the formation of one carbon-nitrogen bond and four carbon-carbon bonds to construct both the aryl and pyrrole rings of the indole in one step.

UR - http://www.scopus.com/inward/record.url?scp=85082820928&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85082820928&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c01057

DO - 10.1021/acs.orglett.0c01057

M3 - Article

C2 - 32237752

AN - SCOPUS:85082820928

SN - 1523-7060

VL - 22

SP - 3268

EP - 3272

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

K₂CO₃-Catalyzed Synthesis of 2,5-Dialkyl-4,6,7-tricyano-Decorated Indoles via Carbon-Carbon Bond Cleavage

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this