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

Anna L. Samsonenko; Anastasia S. Kostyuchenko; Tatyana Yu. Zheleznova; Vladislav Yu. Shuvalov; Igor S. Vlasov; Alexander S. Fisyuk

doi:10.1055/a-1799-9339

Synthesis, Table of Contents

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

Authors

Anna L. Samsonenko

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bFaculty of Chemistry, Silesian University of Technology, Marcina Strzody 9, 44-100 Gliwice, Poland
Anastasia S. Kostyuchenko

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^cDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
Tatyana Yu. Zheleznova

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^cDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
Vladislav Yu. Shuvalov

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^cDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
Igor S. Vlasov

^cDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation
Alexander S. Fisyuk *

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^cDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

Abstract

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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.

Key words

conjugation - cyclization - fused-ring system - heterocycles - amines - azides

Full Text

References

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