Synthesis 2022; 54(14): 3227-3238
DOI: 10.1055/a-1799-9339
paper

Synthesis of New Fused 4H-Thieno[3,2-b]pyrrole Derivatives via Decomposition of Methyl 4-Azido-5-arylthiophene-2-carboxylates

Anna L. Samsonenko
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Faculty of Chemistry, Silesian University of Technology, Marcina Strzody 9, 44-100 Gliwice, Poland
,
Anastasia S. Kostyuchenko
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
c   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
,
Tatyana Yu. Zheleznova
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
c   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
,
Vladislav Yu. Shuvalov
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
c   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
,
Igor S. Vlasov
c   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
,
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
c   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
› Institutsangaben
This work was supported by the Russian Science Foundation (Grant No. 20-73-10043).


Abstract

This article is focused on the development of practical approaches to the synthesis of 4-azido-5-arylthiophene-2-carboxylates and 4-amino-5-arylthiophene-2-carboxylates using the Fiesselmann reaction. The photochemical and thermal (including microwave-assisted) decomposition of 4-azido-5-arylthiophene-2-carboxylates have been studied in order to synthesize fused 4H-thieno[3,2-b]pyrrole derivatives. The proposed approaches allow to obtain functionally substituted heteroacenes, which are of interest as building blocks for organic semiconductors.

Supporting Information



Publikationsverlauf

Eingereicht: 23. Februar 2022

Angenommen nach Revision: 16. März 2022

Accepted Manuscript online:
16. März 2022

Artikel online veröffentlicht:
18. Mai 2022

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