Synthesis of a peralkynylated pyrazino[2,3-g]quinoxaline

Shaobin Miao; Mark D. Smith; Uwe H.F. Bunz

doi:10.1021/ol0529851

Synthesis of a peralkynylated pyrazino[2,3-g]quinoxaline

Shaobin Miao
, Mark D. Smith
, Uwe H.F. Bunz

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

29 Scopus citations

Abstract

The synthesis of a hexaethynyl[2,3-g]pyrazinoquinoxaline and its crystal structure are reported. Starting from tetraaminobenzoquinone, condensation to bis(triisopropylsilyl)hexadiyne-2,3-dione affords 2,3,7,8- tetrakis(triisopropylsilylethynyl)pyrazino[2,3-g]quinoxaline-5,10-dione. Reaction with TIPS-CC-Li followed by reduction with hypophosphite in the presence of KI furnished the title molecule in a yield of 62%. Pd catalysis is not involved in any of these steps.

Original language	English (US)
Pages (from-to)	757-760
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	4
DOIs	https://doi.org/10.1021/ol0529851
State	Published - Feb 16 2006
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of a peralkynylated pyrazino[2,3-g]quinoxaline",

abstract = "The synthesis of a hexaethynyl[2,3-g]pyrazinoquinoxaline and its crystal structure are reported. Starting from tetraaminobenzoquinone, condensation to bis(triisopropylsilyl)hexadiyne-2,3-dione affords 2,3,7,8- tetrakis(triisopropylsilylethynyl)pyrazino[2,3-g]quinoxaline-5,10-dione. Reaction with TIPS-CC-Li followed by reduction with hypophosphite in the presence of KI furnished the title molecule in a yield of 62\%. Pd catalysis is not involved in any of these steps.",

author = "Shaobin Miao and Smith, \{Mark D.\} and Bunz, \{Uwe H.F.\}",

year = "2006",

month = feb,

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doi = "10.1021/ol0529851",

language = "English (US)",

volume = "8",

pages = "757--760",

journal = "Organic Letters",

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T1 - Synthesis of a peralkynylated pyrazino[2,3-g]quinoxaline

AU - Miao, Shaobin

AU - Smith, Mark D.

AU - Bunz, Uwe H.F.

PY - 2006/2/16

Y1 - 2006/2/16

N2 - The synthesis of a hexaethynyl[2,3-g]pyrazinoquinoxaline and its crystal structure are reported. Starting from tetraaminobenzoquinone, condensation to bis(triisopropylsilyl)hexadiyne-2,3-dione affords 2,3,7,8- tetrakis(triisopropylsilylethynyl)pyrazino[2,3-g]quinoxaline-5,10-dione. Reaction with TIPS-CC-Li followed by reduction with hypophosphite in the presence of KI furnished the title molecule in a yield of 62%. Pd catalysis is not involved in any of these steps.

AB - The synthesis of a hexaethynyl[2,3-g]pyrazinoquinoxaline and its crystal structure are reported. Starting from tetraaminobenzoquinone, condensation to bis(triisopropylsilyl)hexadiyne-2,3-dione affords 2,3,7,8- tetrakis(triisopropylsilylethynyl)pyrazino[2,3-g]quinoxaline-5,10-dione. Reaction with TIPS-CC-Li followed by reduction with hypophosphite in the presence of KI furnished the title molecule in a yield of 62%. Pd catalysis is not involved in any of these steps.

UR - https://www.scopus.com/pages/publications/33644777481

UR - https://www.scopus.com/pages/publications/33644777481#tab=citedBy

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SN - 1523-7060

VL - 8

SP - 757

EP - 760

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

Synthesis of a peralkynylated pyrazino[2,3-g]quinoxaline

Abstract

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