Tetracyanoethylene as a building block in the facile synthesis of heteroyl-tetrasubstituted thiazoles

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

doi:10.1007/s00706-020-02669-4

Tetracyanoethylene as a building block in the facile synthesis of heteroyl-tetrasubstituted thiazoles

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

^*Corresponding author for this work

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

2 Scopus citations

Abstract

Abstract: The transformation of N-substituted 2-heteroylthiosemicarbazides to N-(2-substituted imino)-4-amino-5-cyanothiazol-3(2H)-3-yl)-heteroyl-2-carboxamides was achieved via the reaction with tetracyanoethylene, which is used as a building block in this transformation. The structures of the products have been confirmed unambiguously by single-crystal X-ray structure analysis. A rationale for the formation of the products is presented. Graphic abstract: [Figure not available: see fulltext.].

Original language	English
Pages (from-to)	1425-1431
Number of pages	7
Journal	Monatshefte fur Chemie
Volume	151
Issue number	9
DOIs	https://doi.org/10.1007/s00706-020-02669-4
State	Published - 1 Sep 2020
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2020, Springer-Verlag GmbH Austria, part of Springer Nature.

Keywords

2,3,4,5-Tetrasubstituted thiazoles
Donor–acceptor effects
Heterocycles
N-Substituted 2-heteroylthiosemicarbazides
NMR spectroscopy
X-ray structure determination

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1007/s00706-020-02669-4

Cite this

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title = "Tetracyanoethylene as a building block in the facile synthesis of heteroyl-tetrasubstituted thiazoles",

abstract = "Abstract: The transformation of N-substituted 2-heteroylthiosemicarbazides to N-(2-substituted imino)-4-amino-5-cyanothiazol-3(2H)-3-yl)-heteroyl-2-carboxamides was achieved via the reaction with tetracyanoethylene, which is used as a building block in this transformation. The structures of the products have been confirmed unambiguously by single-crystal X-ray structure analysis. A rationale for the formation of the products is presented. Graphic abstract: [Figure not available: see fulltext.].",

keywords = "2,3,4,5-Tetrasubstituted thiazoles, Donor–acceptor effects, Heterocycles, N-Substituted 2-heteroylthiosemicarbazides, NMR spectroscopy, X-ray structure determination",

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

note = "Publisher Copyright: {\textcopyright} 2020, Springer-Verlag GmbH Austria, part of Springer Nature.",

year = "2020",

month = sep,

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doi = "10.1007/s00706-020-02669-4",

language = "English",

volume = "151",

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TY - JOUR

T1 - Tetracyanoethylene as a building block in the facile synthesis of heteroyl-tetrasubstituted thiazoles

AU - Hassan, Alaa A.

AU - Aly, Ashraf A.

AU - Mohamed, Nasr K.

AU - El-Haleem, Lamiaa E.Abd

AU - Bräse, Stefan

AU - Nieger, Martin

PY - 2020/9/1

Y1 - 2020/9/1

N2 - Abstract: The transformation of N-substituted 2-heteroylthiosemicarbazides to N-(2-substituted imino)-4-amino-5-cyanothiazol-3(2H)-3-yl)-heteroyl-2-carboxamides was achieved via the reaction with tetracyanoethylene, which is used as a building block in this transformation. The structures of the products have been confirmed unambiguously by single-crystal X-ray structure analysis. A rationale for the formation of the products is presented. Graphic abstract: [Figure not available: see fulltext.].

AB - Abstract: The transformation of N-substituted 2-heteroylthiosemicarbazides to N-(2-substituted imino)-4-amino-5-cyanothiazol-3(2H)-3-yl)-heteroyl-2-carboxamides was achieved via the reaction with tetracyanoethylene, which is used as a building block in this transformation. The structures of the products have been confirmed unambiguously by single-crystal X-ray structure analysis. A rationale for the formation of the products is presented. Graphic abstract: [Figure not available: see fulltext.].

KW - 2,3,4,5-Tetrasubstituted thiazoles

KW - Donor–acceptor effects

KW - Heterocycles

KW - N-Substituted 2-heteroylthiosemicarbazides

KW - NMR spectroscopy

KW - X-ray structure determination

UR - https://www.scopus.com/pages/publications/85090440293

U2 - 10.1007/s00706-020-02669-4

DO - 10.1007/s00706-020-02669-4

M3 - Article

AN - SCOPUS:85090440293

SN - 0026-9247

VL - 151

SP - 1425

EP - 1431

JO - Monatshefte fur Chemie

JF - Monatshefte fur Chemie

IS - 9

ER -

Tetracyanoethylene as a building block in the facile synthesis of heteroyl-tetrasubstituted thiazoles

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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