A new one-pot acid- and exogenous oxidant-free synthesis of pyrrolo[2,3-c]quinolines has been developed. This strategy involves the chemoselective reduction of 3-(2-nitrophenyl)-1H-pyrroles (pyrrolnitrin derivatives) followed by a DABSO-facilitated Pummerer reaction in the presence of diverse sulfoxides, which enables the formal [5 + 1] heteroannulation of the resultant 3-(2-aminophenyl)-1H-pyrroles (aminopyrrolnitrin derivatives) to give access to the 3H-pyrrolo[2,3-c]quinoline [3H-PQ] scaffold. The present strategy discloses the first example of an SO₂-facilitated Pummerer reaction and facilitates the synthesis of marinoquinoline natural products. Mechanistic investigation including computational studies have been conducted to decipher the underlying mechanism. Also, photophysical investigation of most of the synthesized compounds has been conducted. In addition, antimalarial activity screening revealed potent bioactivity in the micromolar range for some of the synthesized 3H-PQ derivatives.

中文翻译：

---

DABSO 介导的 Pummerer 反应可实现吡咯并喹啉的一锅合成以获得马林喹啉：机理、光物理和药理学研究


已经开发了一种新的无酸和外源性氧化剂合成的吡咯并[2,3-c]喹啉。该策略涉及 3-（2-硝基苯基）-1H-吡咯（吡咯腈衍生物）的化学选择性还原，然后在多种亚砜存在下进行 DABSO 促进的 Pummerer 反应，这使得所得 3-（2-氨基苯基）-1 H-吡咯（氨基吡咯腈衍生物）的正式 [5 + 1] 异氦化成为可能，从而获得 3-（2-氨基苯基）-1H-吡咯[2,3-c]喹啉 [3H-PQ] 支架。本策略公开了 SO₂ 促进的 Pummerer 反应的第一个例子，并促进了马利诺喹啉天然产物的合成。已经进行了包括计算研究在内的机制研究以破译潜在机制。此外，还对大多数合成化合物进行了光物理研究。此外，抗疟活性筛选显示，一些合成的 3H-PQ 衍生物在微摩尔范围内具有强大的生物活性。