Modification of pyrrolo[2,1-a]isoquinolines via dicarbonylation with dimethyl sulfoxide and arylacyl bromides affording 1,2-dicarbonylated pyrrolo[2,1-a]isoquinolines

Modification of Pyrrolo[2,1-a]isoquinolines and Polysubstituted Pyrroles via Methylenation with Acetyl Chloride and Dimethylsulfoxide

“…Since methylthiomethylenation products have been reported as key intermediates by others and us for further transformations, − compound 10 was tested under the optimal conditions. The desired product 2a can be obtained in 67% yield, demonstrating that the methylthiomethylenation product may also be as a crucial intermediate in the current reaction system (eq 3 ).…”

“…3 Later, we developed an efficient dicarbonylation reaction by employing aroyl bromide and DMSO to synthesize 1,2-dicarbonylated pyrroloisoquinolines. 4 DMSO can act as a methylthiomethylating reagent for functionalizing pyrroloisoquinolines in the presence of ammonium acetate. 5 In this reaction system, methylene-bridged pyrroloisoquinolines can be detected in low yields as minor products.…”

“…In our continuing efforts on modifiers of privileged framework-bearing molecules, we found that the combination of ethyl 2-bromoisobutyrate and DMSO can be used for formylation and bromination of pyrroloisoquinolines . Later, we developed an efficient dicarbonylation reaction by employing aroyl bromide and DMSO to synthesize 1,2-dicarbonylated pyrroloisoquinolines . DMSO can act as a methylthiomethylating reagent for functionalizing pyrroloisoquinolines in the presence of ammonium acetate .…”

Pyrrolo[2,1-a]isoquinoline scaffolds for developing anti-cancer agents

“…Developing the pyrroloisoquinoline chemistry, an important modification of pyrrolo[2,1- a ]isoquinolines 145 with arylacyl bromides 146 in the presence of DMSO as oxidant was made via the dicarbonylation reaction which allowed the preparation of 1,2-dicarbonylated pyrroloisoquinolines 145 in acceptable to good yields (12–73%). 70 (Scheme 11). On the other hand, tetrahydroisoquinoline ring is a suitable precursor in the pyrroloisoquinoline chemistry.…”

Modification of Pyrrolo[2,1‐a]isoquinolines through Iron‐Catalyzed Aminomethylenation with Amines and Dimethyl Sulfoxide

“…Previously, we have developed several reaction systems for modification of pyrrolo[2,1-a]isoquinolines by the transformation of DMSO with suitable activators. [13][14][15] Encouraged by recent achievements on developing DMSO-based reaction systems and also based on our own results, we envisioned more diverse functional groups can be incorporated to heterocycles by transforming DMSO with novel activators. As our continuous program on modifying pyrrolo[2,1-a]isoquinolines through DMSO-based approaches and other pathways, we would like to design more DMSO-based reaction systems with novel activators and further produce more structurally complex pyrroloisoquinolines.…”