390410-52-3

Upstream product

• 72486-09-0 methanesulfonic acid but-3-ynyl ester 
• 90-02-8 salicylaldehyde 

Downstream Products

• 390410-53-4 (E)-3-(2-but-3-ynyloxyphenyl)propenal 
• 1257647-30-5 (E)-methyl 2-(benzo[d][1,3]dioxole-5-carbonyl)-3-(2-(but-3-ynyloxy)phenyl)acrylate 
• 390410-57-8 4-(2-but-3-ynyloxyphenyl)but-3-en-2-one N,N-dimethylhydrazone 
• 390410-55-6 (E)-3-(2-but-3-ynyloxyphenyl)propenal N,N-dimethylhydrazone 
• 390410-54-5 (E)-4-(2-but-3-ynyloxyphenyl)but-3-en-2-one 

Relevant academic research and scientific papers

Double intramolecular hetero Diels-Alder reactions of α,β-unsaturated hydrazones as 1-azadienes: A new route to 2,2′-bipyridines

Salicylaldehyde was converted into the O-propynyl- and O-butynyl α,β-unsaturated aldehydes 4 and ketones 6, subsequent reaction of which with N,N-dimethylhydrazine and alkyne homocoupling gave the 1,3-diyne bis-(hydrazones) 8, substrates for a double intramolecular hetero Diels-Alder reaction. Similar substrates 11, 15a/15c and 15b/15d were prepared from 2-(N-benzoylamino)cinnamaldehyde, hex-5-ynol and hept-6-ynol respectively. Heating the 1,3-diynyl bis(α,β-unsaturated hydrazones) 8a, 8c, 11 and 15a resulted in double intramolecular Diels-Alder reaction to give, after aromatisation by loss of dimethylamine, 2,2′-bipyridines 21-24.