TY - JOUR
T1 - Acid-catalyzed reaction of 3-aminopyrrole with s-tetrazines
T2 - Formation of 1H-1,2,4-(triazol-3-yl)pyrimidines via an unprecedented s-tetrazine-ring contraction and concomitant pyrrole-ring expansion
AU - De Rosa, Michael
AU - Arnold, David
AU - Yennawar, Hemant
N1 - Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.
PY - 2014/10/1
Y1 - 2014/10/1
N2 - Initial reaction of 3-aminopyrrole with the conjugate acid of 3,6-diphenyl-1,2,4,5-tetrazine gave an intermediate that rearranged to a 1H-1,2,4-(triazol-3-yl)pyrimidine via an unprecedented cascade. In this cascade, the s-tetrazine-ring opened, contracted to a 1,2,4-triazole-ring, and the pyrrole ring expanded to a pyrimidine. Similar results were obtained with three other electronically different s-tetrazines.
AB - Initial reaction of 3-aminopyrrole with the conjugate acid of 3,6-diphenyl-1,2,4,5-tetrazine gave an intermediate that rearranged to a 1H-1,2,4-(triazol-3-yl)pyrimidine via an unprecedented cascade. In this cascade, the s-tetrazine-ring opened, contracted to a 1,2,4-triazole-ring, and the pyrrole ring expanded to a pyrimidine. Similar results were obtained with three other electronically different s-tetrazines.
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U2 - 10.1016/j.tetlet.2014.08.004
DO - 10.1016/j.tetlet.2014.08.004
M3 - Article
AN - SCOPUS:84910083179
SN - 0040-4039
VL - 55
SP - 5491
EP - 5494
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 40
ER -