Synthesis of new Furo-imidazo[3.3.3]propellanes

Alaa A. Hassan; Nasr K. Mohamed; Lamiaa E. Abd El-Haleem; Stefan Bräse; Martin Nieger

doi:10.2174/1570179412666150513003813

Synthesis of new Furo-imidazo[3.3.3]propellanes

Alaa A. Hassan^*
, Nasr K. Mohamed
, Lamiaa E. Abd El-Haleem
, Stefan Bräse
, Martin Nieger

^*Corresponding author for this work

Research output: Contribution to journal › Review article › peer-review

5 Scopus citations

Abstract

A new class of compounds, namely furo-imidazo-[3.3.3]propellanes can be synthesized by reaction of (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile with N-substituted (2-picolinoyl-, thiophene-2- carbonyl)hydrazinecarbo-thioamides 1a-f. 2,5-Disubstituted-2,3,4-oxadiazoles were also separated from this reaction as a minor product. The structures of products have been confirmed by using IR, NMR, mass spectrometry and single crystal X-ray analyses. A mechanism for the formation of the products is presented.

Original language	English
Pages (from-to)	426-431
Number of pages	6
Journal	Current Organic Synthesis
Volume	13
Issue number	3
DOIs	https://doi.org/10.2174/1570179412666150513003813
State	Published - 1 Jun 2016
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2016 Bentham Science Publishers.

Keywords

2,5- disubstituted-1,3,4-oxadiazoles
Dicyanomethylene-1,3-indanedione
Donor acceptor interactions
Furo-imidazo[3.3.3]propellanes
Hydrazinecarbothioamides
X-ray crystallography

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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10.2174/1570179412666150513003813

Cite this

@article{9f9b1f0e4d7049428e85264895884190,

title = "Synthesis of new Furo-imidazo[3.3.3]propellanes",

abstract = "A new class of compounds, namely furo-imidazo-[3.3.3]propellanes can be synthesized by reaction of (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile with N-substituted (2-picolinoyl-, thiophene-2- carbonyl)hydrazinecarbo-thioamides 1a-f. 2,5-Disubstituted-2,3,4-oxadiazoles were also separated from this reaction as a minor product. The structures of products have been confirmed by using IR, NMR, mass spectrometry and single crystal X-ray analyses. A mechanism for the formation of the products is presented.",

keywords = "2,5- disubstituted-1,3,4-oxadiazoles, Dicyanomethylene-1,3-indanedione, Donor acceptor interactions, Furo-imidazo[3.3.3]propellanes, Hydrazinecarbothioamides, X-ray crystallography",

author = "Hassan, \{Alaa A.\} and Mohamed, \{Nasr K.\} and \{Abd El-Haleem\}, \{Lamiaa E.\} and Stefan Br{\"a}se and Martin Nieger",

note = "Publisher Copyright: {\textcopyright} 2016 Bentham Science Publishers.",

year = "2016",

month = jun,

day = "1",

doi = "10.2174/1570179412666150513003813",

language = "English",

volume = "13",

pages = "426--431",

journal = "Current Organic Synthesis",

issn = "1570-1794",

publisher = "Bentham Science Publishers",

number = "3",

}

TY - JOUR

T1 - Synthesis of new Furo-imidazo[3.3.3]propellanes

AU - Hassan, Alaa A.

AU - Mohamed, Nasr K.

AU - Abd El-Haleem, Lamiaa E.

AU - Bräse, Stefan

AU - Nieger, Martin

PY - 2016/6/1

Y1 - 2016/6/1

N2 - A new class of compounds, namely furo-imidazo-[3.3.3]propellanes can be synthesized by reaction of (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile with N-substituted (2-picolinoyl-, thiophene-2- carbonyl)hydrazinecarbo-thioamides 1a-f. 2,5-Disubstituted-2,3,4-oxadiazoles were also separated from this reaction as a minor product. The structures of products have been confirmed by using IR, NMR, mass spectrometry and single crystal X-ray analyses. A mechanism for the formation of the products is presented.

AB - A new class of compounds, namely furo-imidazo-[3.3.3]propellanes can be synthesized by reaction of (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile with N-substituted (2-picolinoyl-, thiophene-2- carbonyl)hydrazinecarbo-thioamides 1a-f. 2,5-Disubstituted-2,3,4-oxadiazoles were also separated from this reaction as a minor product. The structures of products have been confirmed by using IR, NMR, mass spectrometry and single crystal X-ray analyses. A mechanism for the formation of the products is presented.

KW - 2,5- disubstituted-1,3,4-oxadiazoles

KW - Dicyanomethylene-1,3-indanedione

KW - Donor acceptor interactions

KW - Furo-imidazo[3.3.3]propellanes

KW - Hydrazinecarbothioamides

KW - X-ray crystallography

UR - https://www.scopus.com/pages/publications/84964292711

U2 - 10.2174/1570179412666150513003813

DO - 10.2174/1570179412666150513003813

M3 - Review article

AN - SCOPUS:84964292711

SN - 1570-1794

VL - 13

SP - 426

EP - 431

JO - Current Organic Synthesis

JF - Current Organic Synthesis

IS - 3

ER -

Synthesis of new Furo-imidazo[3.3.3]propellanes

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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