Diastereoselective synthesis of fused [1,3]oxazines from ethyl pyruvate, activated acetylenes and N-heterocycles.
The 1:1 zwitterionic intermediates obtained from the reaction between isoquinoline, quinoline, pyridine, or N-methylimidazole with activated acetylenes are trapped by ethyl pyruvate to produce highly functionalized fused [1,3]oxazines in good yields.
Yavari
Issa
I
Chemistry Department, Tarbiat Modares University, 14115-175, Tehran, Iran. yavarisa@modares.ac.ir
Mirzaei
Anvar
A
Hossaini
Zinatosadat
Z
Souri
Sanaz
S
D000480:Alkynes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry; D007546:Isoquinolines / Q000737:chemistry; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D011773:Pyruvates / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D006571:Heterocyclic Compounds; D007093:Imidazoles; D007546:Isoquinolines; D010078:Oxazines; D011725:Pyridines; D011773:Pyruvates; D011804:Quinolines; C046522:ethyl pyruvate; C023666:pyridine; C018100:1-methylimidazole