Reactivity of thienopyrroles. Synthesis of isomeric nitro and bromothienopyrroles

Abstract

The preparation of ethyl 2‐bromothieno[2,3‐b]pyrrole‐5‐carboxylate, ethyl 2‐bromothieno[3,2‐b]pyrrole‐5‐carboxylate, ethyl 2‐nitrothieno[2,3‐b]pyrrole‐5‐carboxylate and ethyl 2‐nitrothieno[3,2‐b]pyrrole‐5‐carboxylate are described.

Evaluation of thieno[3,2-b]pyrrole[3,2-d]pyridazinones as activators of the tumor cell specific M2 isoform of pyruvate kinase

“…Several commercially available thiophene-2-carbaldehydes were reacted with ethyl 2-azidoacetate in sodium ethoxide at 0 °C to provide the corresponding 2-azido-3-(thiophen-2-yl)acrylates. Refluxing this intermediate in o -xylene provided the core thienopyrroles in good yields 25. Several techniques proved capable of installing the needed aldehyde functionality, but ultimately we relied upon a Vilsmeier-Haack reaction to form the substituted ethyl 6-formyl-4H-thieno[3,2-b]pyrrole-5-carboxylates 26.…”

A 20π‐Electron Heteroporphyrin Containing a Thienopyrrole Unit

“…Planar conformations are normally expected to lead to a destabilization of the π system for porphyrins with (4 n )π‐electron systems. The average displacement of the β‐carbon atoms from the least‐square plane of the meso ‐carbon atoms was 0.093 Å, which is in marked contrast with the 1.36 Å value for [20]isophlorin 13a. It is also noteworthy that the thienopyrrole ring is tilted out of the least‐square plane by only 2.695°, whereas the other three pyrrole rings are tilted by 3.012°, 3.092°, and 7.040°.…”

Trisubstituted Thieno[3,2-b]pyrrole 5-Carboxamides as Potent Inhibitors of Alphaviruses

“…The synthesis of these compounds are summarized in Scheme , starting from thieno­[3,2- b ]­pyrrole ester 5 , which was synthesized following the procedures reported by Eras et al and Srinivasan et al , N-Alkylation of ester 5 with para -methoxy benzyl chloride afforded the desired ester 1 in moderate yield. Saponification of ester 1 gave the corresponding C-5 carboxylic acid 2 .…”