FeCl3-Mediated Three-Component Cascade Reaction: An Effective Approach to the Construction of Highly Functionalized Pyrrolo[1,2-c]quinazolinones

• Published in: Chemistry : a European journal Vol. 20; no. 6; pp. 1711 - 1719
• Main Authors: Zheng, Hu-Fei, Yu, Zhi-Hua, Yuan, Wei, Tang, Zi-Long, Clough, John, Gu, Yu-Cheng, Shi, De-Qing
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 03.02.2014; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Alkaloids - chemical synthesis; Alkaloids - chemistry; allenes; azo compounds; Azo Compounds - chemistry; Chemistry; Chemistry, Multidisciplinary; Cycloaddition Reaction; domino reactions; fused-ring systems; iron; Iron - chemistry; Physical Sciences; Pyrroles - chemistry; Quinazolinones - chemical synthesis; Quinazolinones - chemistry; Science & Technology; Thiosemicarbazones - chemistry; CONVENIENT SYNTHESIS; fused-ring systems; ASYMMETRIC-SYNTHESIS; DIPOLAR DERIVATIVES; ONE-POT SYNTHESIS; azo compounds; AZOMETHINE YLIDES; POTENTIAL 1,3-DIPOLES; 1,3-DIPOLAR CYCLOADDITION REACTIONS; GASTRIC (H+/K+)-ATPASE; allenes; ARYL RADICAL CYCLIZATION; domino reactions; iron; REVERSIBLE INHIBITORS
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201304028

An unexpected FeCl3‐mediated three‐component cascade reaction has been used to construct structurally diverse pyrrolo[1,2‐c]quinazolinone derivatives with potential biological activities. This method has advantages of mild conditions, simple work‐up, as well as wide substrate scope, which makes it a powerful approach to the synthesis of diverse pyrrolo[1,2‐c]quinazolinones. This cascade reaction involves 1,3‐dipolar cycloaddition between azomethine ylides and allenoates, followed by intramolecular nucleophilic addition in the presence of FeCl3. The obtained products could be easily transformed into derivatives with the pyrrolo[2,3‐c]quinazoline alkaloid skeleton. An iron trigger: An FeCl3‐triggered three‐component domino strategy enables access to highly functionalized pyrrolo[1,2‐c]quinazolinones in a single step (see scheme, MS=molecular sieves). The obtained products can be used as building blocks in the synthesis of diverse, potentially biologically active nitrogen‐containing heterocycles. This method features mild conditions, a simple work‐up, as well as a wide substrate scope.