Synthesis of Unsymmetrical Pyrrolo[3,2-b]pyrrole-2,5-diones

Abstract

Synthesis of Unsymmetrical Pyrrolo[3,2-b]pyrrole-2,5-diones S y n t h e s i s o f U n s y m m e t r i c a l P y r r o l o [ 3 , 2 -b ] p y r r o l e -2 , 5 -d i o n e s Abstract: The first unsymmetrical oxalic acid-bis(imidoyl)dichlorides were prepared and applied to the one-pot synthesis of the first unsymmetrical pyrrolo[3,2-b]pyrrole-2,5-diones and 2,2¢-bisquinazolin-4-ones.

Ring-Expanding Reaction of Cyclopropyl Amides with Triphenylphosphine and Carbon Tetrahalide

“…As an initial examination, we found that the reaction of N -phenylcyclopropylamide 1a with 2 equiv of Ph 3 P and 1 equiv of CCl 4 produced the N -phenylpyrrolidin-2-one 3a in 62% yield under reflux for 3 days in acetonitrile (Table SI-1, Supporting Information, entry 1). When we utilized CBr 4 instead of CCl 4 , this reaction proceeded smoothly at 60 °C under similar conditions to give 3a in 97% yield after 3 h. After optimization of the reaction conditions (Table SI-1, Supporting Information), we found that 2 equiv of Ph 3 P and 1 equiv of CBr 4 are required in this reaction to give 3a in good yield and acetonitrile is the best solvent, which is similar to those of other reaction systems using triphenylphosphine and carbon tetrahalide as reagents. , It should be emphasized here that we also attempted to activate cyclopropylamide 1a with PCl 5 and POCl 3 , respectively, typical Vilsmeier−Haack reaction conditions, but the desired product 3a was not formed. At the present stage, we only found that the reagent of PPh 3 /CBr 4 can effectively promote this ring-expanding reaction.…”

Electrochemical polymerization of 1,3,4,6-tetraarylpyrrolo[3,2-b]pyrrole-2,5-dione (isoDPP) derivatives

“…IsoDPP derivatives 1a and 1b were prepared according to the method reported by Langer et al [20][21][22] Details of the synthesis are reported in the literature. 9 Compound 1a was characterized by X-ray analysis of single crystals grown from a benzene solution (see ESI, Fig.…”

Combination of Two Diketopyrrolopyrrole Isomers in One Polymer for Ambipolar Transport

“…The DPP2 was found as a part of the structure of a natural dye in lichens , and was synthesized around 25 years ago . Subsequent studies concentrated on improved synthetic strategies and the preparation of derivatives with different substituents. ,− Until 2011, DPP2 was utilized to synthesize conjugated polymers with a variety of comonomers . Then a series of polymers containing DPP2 in the main chain and their optoelectronic properties were reported in 2012 .…”