122490-12-4

Basic information

• Product Name: 2-ethoxy-4-phenyl-1-aza-1,3-butadiene
• Synonyms: 2-ethoxy-4-phenyl-1-aza-1,3-butadiene
• CAS NO: 122490-12-4
• Molecular Weight: 175.23
• Mol File: 122490-12-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-ethoxy-4-phenyl-1-aza-1,3-butadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ethoxy-4-phenyl-1-aza-1,3-butadiene(122490-12-4)
• EPA Substance Registry System: 2-ethoxy-4-phenyl-1-aza-1,3-butadiene(122490-12-4)

Safety Data

• Hazardous Substances Data: 122490-12-4(Hazardous Substances Data)

Upstream product

• 621-79-4 cinnamamide 
• 368-39-8 triethyloxonium fluoroborate 

Downstream Products

• 122490-31-7 (3aR^*,5S^*,4S^*,7aR^*)-5-methyl-4-phenyl-2,3,3a,6,7,7a-hexahydro-1H-isoindole-1,3-dione 
• 122490-31-7 (3aR^*,5R^*,4S^*,7aR^*)-5-methyl-4-phenyl-2,3,3a,6,7,7a-hexahydro-1H-isoindole-1,3-dione 
• 108306-33-8 (4aR^*,8S^*,8aS^*)-1-ethoxy-8-phenyl-3,4,4a,7,8,8a-hexahydroisoquinol-3-one 
• 108306-33-8 (4aS,8R,8aR)-1-Ethoxy-8-phenyl-4a,7,8,8a-tetrahydro-4H-isoquinolin-3-one 
• 122490-30-6 1-(2(E),4(E)-hexadienoyl)-2-ethoxy-4-phenyl-1-aza-1,3-butadiene 
• 122490-21-5 N-(3,5-hexadienoyl)-2-ethoxy-4-phenyl-1-aza-1,3(E)-butadiene 

Relevant articles and documents

The Intramolecular Diels-Alder Cycloaddition of N-Dienoyl Acrylimidates. An Efficient Approach for the Synthesis of Hexahydroisoquinolones and Hexahydroisoindolones

The intramolecular Diels-Alder reaction of aza trienes featuring the N-acyl vinyl imidate moiety in the chain linking the diene and dienophile has been investigated.The acrylimidate bases 3a-d were synthesized by O-alkylation of the corresponding acrylamides 1a-d followed by deprotonation of imidate salts 2a-d.The imidates were efficiently acylated with 3,5-dienoyl chlorides 5a,e-g in yields ranging from 73 to 87percent.The trienes 6a-g underwent cycloaddition under conditions ranging from 80 to 140 deg C, affording mixtures of cis 7a-g and trans 8a-g hexahydroisoquinolones, respectively, with a preponderance of the cis cycloadduct.The stereochemistry of the major adduct was determined from proton coupling constants and conversion of 7a to the known cis-perhydroisoquinoline 18.The cis stereochemistry is understood to originate from cyloaddition in the prefered endo conformation. 2,4-Hexadienoyl imidates 20a,d also underwent cycloaddition to afford cis hexahydroisoindolones 21a,d and 22a,d.The cycloadducts 7a,e-g were reduced with NaBH4 and NaCNBH3 to the corresponding lactams 24a,e-g.