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Synthesis of β‐Lactam‐Tethered Polycyclic Fused Heterocycles through a Rearrangement by a One‐Pot Tandem [3+2] Cycloaddition Reaction
Author(s) -
Rajesh Raju,
Raghunathan Raghavachary
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201471
Subject(s) - chemistry , cycloaddition , sarcosine , acrylonitrile , isatin , pyrrolidine , azomethine ylide , methyl acrylate , adduct , stereochemistry , tandem , diketone , 1,3 dipolar cycloaddition , combinatorial chemistry , organic chemistry , catalysis , glycine , polymer , amino acid , biochemistry , materials science , copolymer , composite material
Abstract We have developed a one‐pot synthesis of polycyclic fused heterocyclic derivatives by the [3+2] cycloaddition of Baylis–Hillman adducts (BHA) derived from 4‐oxoazetidine‐2‐carbaldehydes as dipolarophiles. The BHA derived from methyl acrylate reacted with the azomethine ylides generated from sarcosine or proline, and the diketone isatin to give unexpected fused polycyclic pyrrolo/pyrrolizinoquinolinone derivatives. The products contain three rings (lactone, pyrrolidine, and lactam) fused at a single C–C junction. Similar reactions carried out with the BHA derived from acrylonitrile gave only the normal mono‐spiro cycloadducts as expected. The dipolarophiles reacted with azomethine ylides generated from other α‐diketones to give polycyclic fused furanopyrrolidine derivatives. The structures of the new heterocycles were confirmed by spectroscopic techniques and unambiguously proved by single‐crystal X‐ray analysis.