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For use of phosgene and its derivatives, see: (a) Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937. (b) Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. J. Org. Chem. 1998, 63, 4802-4807. For use of various carbonates, see: (c) Takeda, K.; Akagi, Y.; Saiki, A.; Tsukahara, T.; Ogura, H. Tetrahedron Lett. 1983, 24, 4569. Izdebski, J.; Pawlak, D. Synthesis 1989, 423. For use of N,N′- carbonyldiimidazole, see: (d) Zhang, X.; Rodrigues, J.; Evans, L.; Hinckle, B.; Ballantyne, L.; Pena, M. J. Org. Chem. 1997, 62, 6420.
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For use of phosgene and its derivatives, see: (a) Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937. (b) Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. J. Org. Chem. 1998, 63, 4802-4807. For use of various carbonates, see: (c) Takeda, K.; Akagi, Y.; Saiki, A.; Tsukahara, T.; Ogura, H. Tetrahedron Lett. 1983, 24, 4569. Izdebski, J.; Pawlak, D. Synthesis 1989, 423. For use of N,N′- carbonyldiimidazole, see: (d) Zhang, X.; Rodrigues, J.; Evans, L.; Hinckle, B.; Ballantyne, L.; Pena, M. J. Org. Chem. 1997, 62, 6420.
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For use of phosgene and its derivatives, see: (a) Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937. (b) Scialdone, M. A.; Shuey, S. W.; Soper, P.; Hamuro, Y.; Burns, D. M. J. Org. Chem. 1998, 63, 4802-4807. For use of various carbonates, see: (c) Takeda, K.; Akagi, Y.; Saiki, A.; Tsukahara, T.; Ogura, H. Tetrahedron Lett. 1983, 24, 4569. Izdebski, J.; Pawlak, D. Synthesis 1989, 423. For use of N,N′-carbonyldiimidazole, see: (d) Zhang, X.; Rodrigues, J.; Evans, L.; Hinckle, B.; Ballantyne, L.; Pena, M. J. Org. Chem. 1997, 62, 6420.
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1,3-Dihydro-2H-benzimidazol-2-ones and related compounds represent attractive families of building blocks having interesting biochemical and pharmacological properties. Regioselective alkylation of 1,3-dihydro-2H-benzimidazol-2-one and structurally related cyclic urea analogues was reported by Meanwell et al. through the use of monoalkoxycarbonyl derivatives (including compound 5). In this paper, 5 was synthesized by treatment of 1,3-dihydrobenzimidazol-2-one with NaH followed by an excess of di-tert-butyl dicarbonate. Meanwell, N. A.; Sit, S. Y.; Gao, J.; Wong, H. S.; Gao, Q.; St Laurent, D. R.; Balasubramanian, N. J. Org. Chem. 1995, 60, 1565.
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It is noteworthy that for the synthesis of oligoanthranilamides the group of Hamilton used 2-nitrobenzoic acid in place of N-benzoylanthranilic acid. In this case, the nitro group as a masked form of the amine was required to avoid the formation of azlactone: Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1996, 118, 7529.
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note
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3-i-Pr (9).
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29
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