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The synthesis of a 5,7-membered fused-ring compound by a tandem Pummerer rearrangement and intramolecular [4+3] cycloaddition

✍ Scribed by Youhong Hu; Ligong Ou; Donglu Bai

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
184 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

A 5, 7-membered fused-ring compound with a fianctionalized angular substituent, 8-methoxy-8act-methoxymethyl-7-phenylthio-1, 2, 3, 6-tetrahydro-3acq 613-epoxyazulene, was synthesized via a tandem Pummerer rearrangement and intramolecular [4+3] cycloaddition.

πŸ“œ SIMILAR VOLUMES

Diastereoselective intramolecular [4+3]
Diastereoselective intramolecular [4+3] cycloaddition: Synthesis of a versatile precursor for preparation of 5,7-fused ring compounds
✍ Ligong Ou; Youhong Hu; Guoqiang Song; Donglu Bai πŸ“‚ Article πŸ“… 1999 πŸ› Elsevier Science 🌐 French βš– 302 KB

Compound 8 which could be used as a versatile precursor for the synthesis of 5,7membered fused ring containing natural products was synthesized via tandem Pummerer rearrangement and intramolecular [4+3] cycloaddition in moderate yield and with high diastereoselectivity.

2-Butyl-5-chloro-3H-imidazole-4-carbalde
2-Butyl-5-chloro-3H-imidazole-4-carbaldehyde as a new synthon for the synthesis of fused ring heterocycles via intramolecular 1,3-dipolar cycloaddition reactions
✍ S. L. Gaonkar; K. M. Lokanatha Rai πŸ“‚ Article πŸ“… 2010 πŸ› Journal of Heterocyclic Chemistry 🌐 English βš– 81 KB πŸ‘ 1 views

## Abstract magnified image The title compound 2‐butyl‐5‐chloro‐3__H__‐imidazole‐4‐carbaldehyde was transformed into tricyclic heterocycles by substituting the chlorine atom by an unsaturated thiolate or alkoxide and then converting aldehyde function into 1,3‐dipole. Chloramine‐T was used as an ef