Dimrothni qayta qurish - Dimroth rearrangement

The Dimrothni qayta qurish a qayta tashkil etish reaktsiyasi aniq bilan sodir bo'lmoqda 1,2,3-triazollar qayerda endotsiklik va ekzosiklik azot atomlar o'rnini almashtiradi.[1] Bu organik reaktsiya tomonidan 1909 yilda kashf etilgan Otto Dimrot.[2][3][4]

Dimrothni qayta qurish

R a bilan fenil guruh reaktsiyasi qaynash jarayonida sodir bo'ladi piridin 24 soat davomida.[5]

Ushbu turdagi triazol an amino 5 pozitsiyasida guruh. A ga qo'ng'iroq ochilgandan keyin diazo protonning 1,3-migratsiyasi bilan oraliq, C-C bog'lanish aylanishi mumkin.

Muayyan 1-alkil-2-iminopirimidinlar shuningdek, ushbu turdagi qayta tashkil etishni namoyish eting.

Pirimidin Dimrot

Birinchi qadamda qo'shilish reaktsiyasi suvdan keyin halqaning ochilishi gemaminali aminoaldegidga, so'ngra halqa yopilishiga.

Adabiyotlar

  1. ^ Heterosiklik kimyo T.L. Gilxrist ISBN  0-582-01421-2
  2. ^ Ueber intramolekulare Umlagerungen. Umlagerungen in der Reihe des 1, 2, 3-Triazollar Yustus Libebigning "Annalen der Chemie" asari 364-jild, 2-son, sana: 1909, Sahifalar: 183-226 Otto Dimrot doi:10.1002 / jlac.19093640204
  3. ^ Intramolekulare Umlagerung der 5-Amino-1,2,3-triazol Yustus Libebigning "Annalen der Chemie" asari 459-jild, 1-son, sana: 1927, Sahifalar: 39-46 Otto Dimroth, Valter Michaelis doi:10.1002 / jlac.19274590104
  4. ^ Mittheilungen Ueber eine Synthese von Derivaten des 1.2.3-Triazols Otto Dimrot Berichte der deutschen chemischen Gesellschaft 1902 35-jild, 1-son, 1029 - 1038-betlar doi:10.1002 / cber.190203501171
  5. ^ Organik sintezlar, Coll. Vol. 4, s.380 (1963); Vol. 37, s.26 (1957). http://orgsynth.org/orgsyn/pdfs/CV4P0380.pdf