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82. Thermal cyclization of 3-azido-2-phenyl-indan-1-one to 5H-indeno[1,2-b]indol-10-one(Organic Azides in Heterocyclic Synthesis, Part 29)
Stadlbauer W., Fischer M., J. Heterocyclic Chem. 39,, 131-135 (2002).

Abstract: 3-Azido-2-phenylindan-1-one, which was obtained from 3-chloro-2-phenylindan-1-one, cyclizes on thermolysis to 5H-indeno[1,2-b]indol-10-one. The reaction conditions were investigated by DSC (differential scanning calorimetry). Reaction of 3-azido-2-phenylindan-1-one with triphenylphosphane gives 2-phenyl-3-(triphenylphosphoranylideneamino)-indan-1-one, which can be hydrolyzed to 3-amino-2-phenylindan-1-one. Attempts to perform a similar cyclization sequence with 3-chloro-2-pyridylindan-1-ones failed.


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