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Related method: (a) Molina, P.; Alajarin, M.; Vidal, A.; Foces-Foces, M. C.; Hernández-Cano, F. Tetrahedron 1989, 45, 4263. (b) Villalgordo, J. M.; Obrecht, D.; Chucholowsky, A. Synlett 1998, 1405.
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0001003013
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Related method: (a) Molina, P.; Alajarin, M.; Vidal, A.; Foces- Foces, M. C.; Hernández-Cano, F. Tetrahedron 1989, 45, 4263. (b) Villalgordo, J. M.; Obrecht, D.; Chucholowsky, A. Synlett 1998, 1405.
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0032512605
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For problems found in this type of deprotection, see: Buenadicha, F. L.; Bartolomé, M. T.; Aguirre, M. J.; Avendaño, C.; Söllhuber, M. Tetrahedron: Asymmetry 1998, 9, 483.
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0033582664
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Treatment with piperidine to give an amidine carboxamide, followed by silica gel-induced cyclization to a 2-aminomethyl-3-carboxymethyl-3,4-dihydroquinazolin-4-one and then to the tricyclic system: He, F.; Snider, B. B. J. Org. Chem. 1999, 64, 1397. For an alternative method to achieve this cyclization, in the context of a synthesis of the alkaloid (-)-alantrypinone, see: Hart, D. J.; Magomedov, N. Tetrahedron Lett. 1999, 40, 5429.
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0033166696
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Treatment with piperidine to give an amidine carboxamide, followed by silica gel-induced cyclization to a 2-aminomethyl-3- carboxymethyl-3,4-dihydroquinazolin-4-one and then to the tricyclic system: He, F.; Snider, B. B. J. Org. Chem. 1999, 64, 1397. For an alternative method to achieve this cyclization, in the context of a synthesis of the alkaloid (-)-alantrypinone, see: Hart, D. J.; Magomedov, N. Tetrahedron Lett. 1999, 40, 5429.
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Use of higher pressures (4 atm) favors the cyclization of compounds 4 to the corresponding 2,5-piperazinediones.
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