Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes: [4 + 2] Cycloaddition Reaction of Amidines with 1,3,5-Triazines

• Published in: Journal of organic chemistry Vol. 59; no. 17; pp. 4950 - 4955
• Main Authors: Boger, Dale L, Kochanny, Monica J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.08.1994; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; 1,2,4-TRIAZINES; ACID; THERMAL CYCLOADDITION; DIMETHYL "1,2,4,5-TETRAZINE-3,6-DICARBOXYLATE; STREPTONIGRIN; PYRIMIDINES; DIENOPHILES; CYCLO-ADDITION; FORMAL TOTAL SYNTHESIS; METHYL-ESTER

A detailed study of the scope of the amidine Diels-Alder reaction with 1,3,5-triazines is described. The thermal reaction of amidines with symmetrical 1,3,5-triazines proceeds with in situ amidine to 1,1-diaminoethene tautomerization, [4 + 2] cycloaddition with the 1,3,5-triazine, loss of ammonia fr...