Understanding the tetrazole ring cleavage reaction with hydrazines: Structural determination and mechanistic insight

作者：Shyyka Olga Ya^*; Pokhodylo Nazariy T; Slyvka Yurii I; Goreshnik Evgeny A; Obushak Mykola D

来源：Tetrahedron Letters, 2018, 59(12): 1112-1115.

DOI：10.1016/j.tetlet.2018.02.016

• 1H-Tetrazole
• Hydrazines
• Thieno[2,3-d]pyrimidin-4(3H)-ones
• Thieno[3,2-d]pyrimidin-4(3H)-ones
• [1]Benzofuro[3,2-d]pyrimidin-4(3H)-one
• Regioselectivity

A distinction in the behaviour of several hydrazines as N-nucleophiles in the recently developed one-pot method for pyrimidine core annulation via 1H-tetrazole ring cleavage was examined. The product structures, 2,3-diamino- or hydrazino derivatives of thieno[3,2-d]pyrimidin-4(3H)-ones, thieno[2,3-d]pyrimidin-4(3H)-ones and [1]benzofuro[3,2-d]pyrimidin-4(3H)-one, were elucidated based on NMR and single crystal X-ray analysis.

• 出版日期2018-3-21