Synthesis of Novel Trispiroheterocycles through 1,3-Dipolar Cycloaddition of Azomethine Ylides and Nitrile Oxide

• Published in: Chinese journal of chemistry Vol. 28; no. 3; pp. 434 - 438
• Main Authors: Li, Xiaofang, Yu, Xianyong, Yi, Pinggui
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.03.2010; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: 1,3‐dipolar cycloaddition; 3-dipolar cycloaddition; azomethine ylide; Chemistry; Chemistry, Multidisciplinary; nitrile oxide; Physical Sciences; Science & Technology; spiroheterocycle; spiroheterocycle; azomethine ylide; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; nitrile oxide; SPIRO; DISCOVERY; 1,3-dipolar cycloaddition
• ISSN: 1001-604X; 1614-7065
• DOI: 10.1002/cjoc.201090092

The 1,3‐dipolar cycloaddition of an azomethine ylide generated by a decarboxylative route from sarcosine and isatin to 1‐benzyl‐3,5‐diarylmethylidene‐piperidin‐4‐ones afforded novel di‐spiro‐indolo/pyrrolidino/piperidines in moderate yields. Further cycloaddition of these di‐spiro compounds to nitrile oxide afforded tri‐spiro‐indolo/pyrrolidino/piperadino/isoxazolines in moderate yields with high regio‐ and stereoselectivity. The 1,3‐dipolar cycloaddition of an azomethine ylide to 1‐benzyl‐3,5‐diarylmethylidene‐piperidin‐4‐ones afforded novel di‐spiro indolo/pyrrolidino/piperidines in moderate yields. Further cycloaddition of these di‐spiro compounds to nitrile oxide afforded tri‐spiro‐indolo/pyrrolidino/piperadino/isoxazolines in moderate yields with high regio‐ and stereoselectivity.