One-pot reactions of N-(mesyloxy)phthalimides with secondary amines to 2-ureidobenzamides, 2-ureidobenzoic acids, ethyl 2-ureidobenzoates, or isatoic anhydrides

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5109-5115

  Gütschow, Michael ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 UREIDOBENZAMIDE; 2 UREIDOBENZOIC ACID; 2 UREIDOBENZOIC ACID ETHYL ESTER; BENZAMIDE DERIVATIVE; PHTHALIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; DEACYLATION; DRUG SYNTHESIS; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 0038761764     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9900634     Document Type: Article

References (49)

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12. Other synthetic routes to I (R, R′ ≠ H): (a) From anthranilic acid via 2-benzotriazolyl-4H-3,1- benzoxazin-4-one: Butula, I.; Vela, V.; Zorc, B. Croat. Chem. Acta 1981, 54, 105. (b) From isatoic anhydride via 2-isothiocyanatobenzoyl chloride: Ulrich, H.; Tucker, B.; Sayigh, A. A. R. J. Org. Chem. 1967, 32, 4052. (c) From methyl 2-aminobenzoate via 2-methoxycarbonylphenylcarbamoyl chloride: ref 1. (d) From methyl 2-aminobenzoate and phosgene-iminium salts: Bitter, I.; Szöcs. L.; Töke, L. Acta Chim. Acad. Hung. 1981, 107, 57.
13. Other synthetic routes to I (R, R′ ≠ H): (a) From anthranilic acid via 2-benzotriazolyl-4H-3,1- benzoxazin-4-one: Butula, I.; Vela, V.; Zorc, B. Croat. Chem. Acta 1981, 54, 105. (b) From isatoic anhydride via 2-isothiocyanatobenzoyl chloride: Ulrich, H.; Tucker, B.; Sayigh, A. A. R. J. Org. Chem. 1967, 32, 4052. (c) From methyl 2-aminobenzoate via 2-methoxycarbonylphenylcarbamoyl chloride: ref 1. (d) From methyl 2-aminobenzoate and phosgene-iminium salts: Bitter, I.; Szöcs. L.; Töke, L. Acta Chim. Acad. Hung. 1981, 107, 57.
14. Other synthetic routes to I (R, R′ ≠ H): (a) From anthranilic acid via 2-benzotriazolyl-4H-3,1- benzoxazin-4-one: Butula, I.; Vela, V.; Zorc, B. Croat. Chem. Acta 1981, 54, 105. (b) From isatoic anhydride via 2-isothiocyanatobenzoyl chloride: Ulrich, H.; Tucker, B.; Sayigh, A. A. R. J. Org. Chem. 1967, 32, 4052. (c) From methyl 2-aminobenzoate via 2-methoxycarbonylphenylcarbamoyl chloride: ref 1. (d) From methyl 2-aminobenzoate and phosgene-iminium salts: Bitter, I.; Szöcs. L.; Töke, L. Acta Chim. Acad. Hung. 1981, 107, 57.
15. Other synthetic routes to I (R, R′ ≠ H): (a) From anthranilic acid via 2-benzotriazolyl-4H-3,1- benzoxazin-4-one: Butula, I.; Vela, V.; Zorc, B. Croat. Chem. Acta 1981, 54, 105. (b) From isatoic anhydride via 2-isothiocyanatobenzoyl chloride: Ulrich, H.; Tucker, B.; Sayigh, A. A. R. J. Org. Chem. 1967, 32, 4052. (c) From methyl 2-aminobenzoate via 2-methoxycarbonylphenylcarbamoyl chloride: ref 1. (d) From methyl 2-aminobenzoate and phosgene-iminium salts: Bitter, I.; Szöcs. L.; Töke, L. Acta Chim. Acad. Hung. 1981, 107, 57.
16. The reaction of isatoic anhydrides with amines (or alcohols) produce two different types of products, 2-aminobenzamides (or alkyl esters) and 2-ureidobenzoic acids (or 2-alkoxycarbonylaminobenzoic acids) depending on the nucleophile and the reaction conditions. For examples see: (a) Staiger, R. P.; Wagner, E. C. J. Org. Chem. 1953, 18, 1427. (b) Bunnett, J. F.; Naff, M. B. J. Am. Chem. Soc. 1966, 88, 4001. (c) Hegarty, A. F.; Ahern, E. P.; Frost, L. N.; Hegarthy, C. N. J. Chem. Soc., Perkin Trans. 2 1990, 1935. (d) Coppola, G. M. Synthesis 1980, 505. (e) Kappe, T.; Stadlbauer, W. Adv. Heterocycl. Chem. 1981, 28, 127. (f) Heyman, D. J. Heterocycl. Chem. 1978, 15, 1131. (g) Hinman, C.; Vaughan, K. Synthesis 1980, 719.
17. The reaction of isatoic anhydrides with amines (or alcohols) produce two different types of products, 2-aminobenzamides (or alkyl esters) and 2-ureidobenzoic acids (or 2-alkoxycarbonylaminobenzoic acids) depending on the nucleophile and the reaction conditions. For examples see: (a) Staiger, R. P.; Wagner, E. C. J. Org. Chem. 1953, 18, 1427. (b) Bunnett, J. F.; Naff, M. B. J. Am. Chem. Soc. 1966, 88, 4001. (c) Hegarty, A. F.; Ahern, E. P.; Frost, L. N.; Hegarthy, C. N. J. Chem. Soc., Perkin Trans. 2 1990, 1935. (d) Coppola, G. M. Synthesis 1980, 505. (e) Kappe, T.; Stadlbauer, W. Adv. Heterocycl. Chem. 1981, 28, 127. (f) Heyman, D. J. Heterocycl. Chem. 1978, 15, 1131. (g) Hinman, C.; Vaughan, K. Synthesis 1980, 719.
18. The reaction of isatoic anhydrides with amines (or alcohols) produce two different types of products, 2-aminobenzamides (or alkyl esters) and 2-ureidobenzoic acids (or 2-alkoxycarbonylaminobenzoic acids) depending on the nucleophile and the reaction conditions. For examples see: (a) Staiger, R. P.; Wagner, E. C. J. Org. Chem. 1953, 18, 1427. (b) Bunnett, J. F.; Naff, M. B. J. Am. Chem. Soc. 1966, 88, 4001. (c) Hegarty, A. F.; Ahern, E. P.; Frost, L. N.; Hegarthy, C. N. J. Chem. Soc., Perkin Trans. 2 1990, 1935. (d) Coppola, G. M. Synthesis 1980, 505. (e) Kappe, T.; Stadlbauer, W. Adv. Heterocycl. Chem. 1981, 28, 127. (f) Heyman, D. J. Heterocycl. Chem. 1978, 15, 1131. (g) Hinman, C.; Vaughan, K. Synthesis 1980, 719.
19. The reaction of isatoic anhydrides with amines (or alcohols) produce two different types of products, 2-aminobenzamides (or alkyl esters) and 2-ureidobenzoic acids (or 2-alkoxycarbonylaminobenzoic acids) depending on the nucleophile and the reaction conditions. For examples see: (a) Staiger, R. P.; Wagner, E. C. J. Org. Chem. 1953, 18, 1427. (b) Bunnett, J. F.; Naff, M. B. J. Am. Chem. Soc. 1966, 88, 4001. (c) Hegarty, A. F.; Ahern, E. P.; Frost, L. N.; Hegarthy, C. N. J. Chem. Soc., Perkin Trans. 2 1990, 1935. (d) Coppola, G. M. Synthesis 1980, 505. (e) Kappe, T.; Stadlbauer, W. Adv. Heterocycl. Chem. 1981, 28, 127. (f) Heyman, D. J. Heterocycl. Chem. 1978, 15, 1131. (g) Hinman, C.; Vaughan, K. Synthesis 1980, 719.
20. The reaction of isatoic anhydrides with amines (or alcohols) produce two different types of products, 2-aminobenzamides (or alkyl esters) and 2-ureidobenzoic acids (or 2-alkoxycarbonylaminobenzoic acids) depending on the nucleophile and the reaction conditions. For examples see: (a) Staiger, R. P.; Wagner, E. C. J. Org. Chem. 1953, 18, 1427. (b) Bunnett, J. F.; Naff, M. B. J. Am. Chem. Soc. 1966, 88, 4001. (c) Hegarty, A. F.; Ahern, E. P.; Frost, L. N.; Hegarthy, C. N. J. Chem. Soc., Perkin Trans. 2 1990, 1935. (d) Coppola, G. M. Synthesis 1980, 505. (e) Kappe, T.; Stadlbauer, W. Adv. Heterocycl. Chem. 1981, 28, 127. (f) Heyman, D. J. Heterocycl. Chem. 1978, 15, 1131. (g) Hinman, C.; Vaughan, K. Synthesis 1980, 719.
21. The reaction of isatoic anhydrides with amines (or alcohols) produce two different types of products, 2-aminobenzamides (or alkyl esters) and 2-ureidobenzoic acids (or 2-alkoxycarbonylaminobenzoic acids) depending on the nucleophile and the reaction conditions. For examples see: (a) Staiger, R. P.; Wagner, E. C. J. Org. Chem. 1953, 18, 1427. (b) Bunnett, J. F.; Naff, M. B. J. Am. Chem. Soc. 1966, 88, 4001. (c) Hegarty, A. F.; Ahern, E. P.; Frost, L. N.; Hegarthy, C. N. J. Chem. Soc., Perkin Trans. 2 1990, 1935. (d) Coppola, G. M. Synthesis 1980, 505. (e) Kappe, T.; Stadlbauer, W. Adv. Heterocycl. Chem. 1981, 28, 127. (f) Heyman, D. J. Heterocycl. Chem. 1978, 15, 1131. (g) Hinman, C.; Vaughan, K. Synthesis 1980, 719.
22. The reaction of isatoic anhydrides with amines (or alcohols) produce two different types of products, 2-aminobenzamides (or alkyl esters) and 2-ureidobenzoic acids (or 2-alkoxycarbonylaminobenzoic acids) depending on the nucleophile and the reaction conditions. For examples see: (a) Staiger, R. P.; Wagner, E. C. J. Org. Chem. 1953, 18, 1427. (b) Bunnett, J. F.; Naff, M. B. J. Am. Chem. Soc. 1966, 88, 4001. (c) Hegarty, A. F.; Ahern, E. P.; Frost, L. N.; Hegarthy, C. N. J. Chem. Soc., Perkin Trans. 2 1990, 1935. (d) Coppola, G. M. Synthesis 1980, 505. (e) Kappe, T.; Stadlbauer, W. Adv. Heterocycl. Chem. 1981, 28, 127. (f) Heyman, D. J. Heterocycl. Chem. 1978, 15, 1131. (g) Hinman, C.; Vaughan, K. Synthesis 1980, 719.
23. N-(Mesyloxy)phthalimide was reported to react with piperidine to the analogue 2-ureidobenzamide derivative; see ref 14.
24. Kühle, E.; Wegler, R. Liebigs Ann. Chem. 1958, 616, 183.
25. The reaction of N-(sulfonyloxy)phthalimides with primary amines as well as O-, S-, and C-nucleophiles has widely been utilized in organic syntheses. For examples, see: (a) Bauer, L.; Exner, O. Angew. Chem., Int. Ed. Engl. 1974, 13, 376. (b) Fahmy, A., F. M.; Aly, N. F.; Nada, A.; Aly, N. Y. Bull. Chem. Soc. Jpn. 1977, 50, 2678. (c) Fahmy, A. F. M.; Aly, N. F.; Orabi, M. O. Bull. Chem. Soc. Jpn. 1978, 150, 2148. (d) Gütschow, M.; Tonew, E.; Leistner, S. Pharmazie 1995, 50, 672. (e) Chapman, T. M.; Freedman, E. A. J. Org. Chem. 1973, 38, 3908. (f) Sheradsky, T.; Itzhak, N. J. Chem. Soc., Perkin Trans. 1 1986, 13. See also ref 14. For an application of the Lossen rearrangement of N-(sulfonyloxy)phthalimides in the design of mechanism-based inhibitors of serine proteases, see ref 16.
26. The reaction of N-(sulfonyloxy)phthalimides with primary amines as well as O-, S-, and C-nucleophiles has widely been utilized in organic syntheses. For examples, see: (a) Bauer, L.; Exner, O. Angew. Chem., Int. Ed. Engl. 1974, 13, 376. (b) Fahmy, A., F. M.; Aly, N. F.; Nada, A.; Aly, N. Y. Bull. Chem. Soc. Jpn. 1977, 50, 2678. (c) Fahmy, A. F. M.; Aly, N. F.; Orabi, M. O. Bull. Chem. Soc. Jpn. 1978, 150, 2148. (d) Gütschow, M.; Tonew, E.; Leistner, S. Pharmazie 1995, 50, 672. (e) Chapman, T. M.; Freedman, E. A. J. Org. Chem. 1973, 38, 3908. (f) Sheradsky, T.; Itzhak, N. J. Chem. Soc., Perkin Trans. 1 1986, 13. See also ref 14. For an application of the Lossen rearrangement of N-(sulfonyloxy)phthalimides in the design of mechanism-based inhibitors of serine proteases, see ref 16.
27. The reaction of N-(sulfonyloxy)phthalimides with primary amines as well as O-, S-, and C-nucleophiles has widely been utilized in organic syntheses. For examples, see: (a) Bauer, L.; Exner, O. Angew. Chem., Int. Ed. Engl. 1974, 13, 376. (b) Fahmy, A., F. M.; Aly, N. F.; Nada, A.; Aly, N. Y. Bull. Chem. Soc. Jpn. 1977, 50, 2678. (c) Fahmy, A. F. M.; Aly, N. F.; Orabi, M. O. Bull. Chem. Soc. Jpn. 1978, 150, 2148. (d) Gütschow, M.; Tonew, E.; Leistner, S. Pharmazie 1995, 50, 672. (e) Chapman, T. M.; Freedman, E. A. J. Org. Chem. 1973, 38, 3908. (f) Sheradsky, T.; Itzhak, N. J. Chem. Soc., Perkin Trans. 1 1986, 13. See also ref 14. For an application of the Lossen rearrangement of N-(sulfonyloxy)phthalimides in the design of mechanism-based inhibitors of serine proteases, see ref 16.
28. The reaction of N-(sulfonyloxy)phthalimides with primary amines as well as O-, S-, and C-nucleophiles has widely been utilized in organic syntheses. For examples, see: (a) Bauer, L.; Exner, O. Angew. Chem., Int. Ed. Engl. 1974, 13, 376. (b) Fahmy, A., F. M.; Aly, N. F.; Nada, A.; Aly, N. Y. Bull. Chem. Soc. Jpn. 1977, 50, 2678. (c) Fahmy, A. F. M.; Aly, N. F.; Orabi, M. O. Bull. Chem. Soc. Jpn. 1978, 150, 2148. (d) Gütschow, M.; Tonew, E.; Leistner, S. Pharmazie 1995, 50, 672. (e) Chapman, T. M.; Freedman, E. A. J. Org. Chem. 1973, 38, 3908. (f) Sheradsky, T.; Itzhak, N. J. Chem. Soc., Perkin Trans. 1 1986, 13. See also ref 14. For an application of the Lossen rearrangement of N-(sulfonyloxy)phthalimides in the design of mechanism-based inhibitors of serine proteases, see ref 16.
29. The reaction of N-(sulfonyloxy)phthalimides with primary amines as well as O-, S-, and C-nucleophiles has widely been utilized in organic syntheses. For examples, see: (a) Bauer, L.; Exner, O. Angew. Chem., Int. Ed. Engl. 1974, 13, 376. (b) Fahmy, A., F. M.; Aly, N. F.; Nada, A.; Aly, N. Y. Bull. Chem. Soc. Jpn. 1977, 50, 2678. (c) Fahmy, A. F. M.; Aly, N. F.; Orabi, M. O. Bull. Chem. Soc. Jpn. 1978, 150, 2148. (d) Gütschow, M.; Tonew, E.; Leistner, S. Pharmazie 1995, 50, 672. (e) Chapman, T. M.; Freedman, E. A. J. Org. Chem. 1973, 38, 3908. (f) Sheradsky, T.; Itzhak, N. J. Chem. Soc., Perkin Trans. 1 1986, 13. See also ref 14. For an application of the Lossen rearrangement of N-(sulfonyloxy)phthalimides in the design of mechanism-based inhibitors of serine proteases, see ref 16.
30. The reaction of N-(sulfonyloxy)phthalimides with primary amines as well as O-, S-, and C-nucleophiles has widely been utilized in organic syntheses. For examples, see: (a) Bauer, L.; Exner, O. Angew. Chem., Int. Ed. Engl. 1974, 13, 376. (b) Fahmy, A., F. M.; Aly, N. F.; Nada, A.; Aly, N. Y. Bull. Chem. Soc. Jpn. 1977, 50, 2678. (c) Fahmy, A. F. M.; Aly, N. F.; Orabi, M. O. Bull. Chem. Soc. Jpn. 1978, 150, 2148. (d) Gütschow, M.; Tonew, E.; Leistner, S. Pharmazie 1995, 50, 672. (e) Chapman, T. M.; Freedman, E. A. J. Org. Chem. 1973, 38, 3908. (f) Sheradsky, T.; Itzhak, N. J. Chem. Soc., Perkin Trans. 1 1986, 13. See also ref 14. For an application of the Lossen rearrangement of N-(sulfonyloxy)phthalimides in the design of mechanism-based inhibitors of serine proteases, see ref 16.
31. Neumann, U.; Gütschow, M. J. Biol. Chem. 1994, 269, 21561.
32. For a review on E1cB processes in acyl transfer reactions, see: Williams, A.; Douglas, K. T. Chem. Rev. 1975, 75, 627. See also: Gütschow, M.; Hecker, T.; Eger, K. Synthesis 1999, 410.
33. For a review on E1cB processes in acyl transfer reactions, see: Williams, A.; Douglas, K. T. Chem. Rev. 1975, 75, 627. See also: Gütschow, M.; Hecker, T.; Eger, K. Synthesis 1999, 410.
34. For the formation of mesoionic quinazolines from 2-isocyanatobenzamides, see ref 14.
35. 2 (≈-2): Collumeau, A. Bull. Soc. Chim. Fr. 1968, 5087.
36. For the interdependence of intramolecular hydrogen bonding and intramolecular general catalysis, see: (a) Benkovic, S. J., Dunikoski, L. K., Jr. Biochemistry 1970, 9, 1390. For intramolecular acid catalysis of the hydrolysis of 3,1-benzoxazin-4-ones by a neighboring carboxyl group, see: (b) Hegarty, A. F.; Pratt, R. F.; Giudici, T.; Bruice, T. C. J. Am. Chem. Soc. 1971, 93, 1428. (c) Cremin, D. J.; Hegarty, A. F. J. Chem. Soc., Perkin Trans. 2 1978, 208.
37. For the interdependence of intramolecular hydrogen bonding and intramolecular general catalysis, see: (a) Benkovic, S. J., Dunikoski, L. K., Jr. Biochemistry 1970, 9, 1390. For intramolecular acid catalysis of the hydrolysis of 3,1-benzoxazin-4-ones by a neighboring carboxyl group, see: (b) Hegarty, A. F.; Pratt, R. F.; Giudici, T.; Bruice, T. C. J. Am. Chem. Soc. 1971, 93, 1428. (c) Cremin, D. J.; Hegarty, A. F. J. Chem. Soc., Perkin Trans. 2 1978, 208.
38. For the interdependence of intramolecular hydrogen bonding and intramolecular general catalysis, see: (a) Benkovic, S. J., Dunikoski, L. K., Jr. Biochemistry 1970, 9, 1390. For intramolecular acid catalysis of the hydrolysis of 3,1-benzoxazin-4-ones by a neighboring carboxyl group, see: (b) Hegarty, A. F.; Pratt, R. F.; Giudici, T.; Bruice, T. C. J. Am. Chem. Soc. 1971, 93, 1428. (c) Cremin, D. J.; Hegarty, A. F. J. Chem. Soc., Perkin Trans. 2 1978, 208.
39. Relevant NOE enhancements in 4 and 11: (Formula Presented)
40. Isatoic anhydride was obtained from benzoic acids with an adjacent carbamate residue under basic conditions or on thermal treatment: (a) Frost, L. N.; Hegarty, A. F. J. Chem. Soc., Chem. Commun. 1973, 82. (b) Hegarty, A. F.; Frost, L. N.; Cremin, D. J. Chem. Soc., Perkin Trans. 2 1974, 1249. See also ref 12f.
41. Isatoic anhydride was obtained from benzoic acids with an adjacent carbamate residue under basic conditions or on thermal treatment: (a) Frost, L. N.; Hegarty, A. F. J. Chem. Soc., Chem. Commun. 1973, 82. (b) Hegarty, A. F.; Frost, L. N.; Cremin, D. J. Chem. Soc., Perkin Trans. 2 1974, 1249. See also ref 12f.
42. 2Et, CONRR′, and Me, respectively, and compared to the observed values. The shift differences were 0.77-0.85 ppm for 2-ureidobenzamides (4, 5, 7-10), 1.09-1.19 ppm for 2-ureidobenzoic acids (11-14), and 1.16-1.32 ppm for ethyl 2-ureidobenzoates (15-18).
43. Iwata, C.; Watanabe, M.; Okamoto, S.; Fujimoto, M.; Sakae, M.; Katsurada, M., Imanishi, T. Heterocycles 1988, 27, 323.
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45. Newman, M. S.; Lord, B. T. J. Am. Chem, Soc. 1944, 66, 733.
46. + - NRR′ - HNRR′).
47. + - HNRR′ - NRR′).
48. Clark, R. H.; Wagner, E. C. J. Org. Chem. 1944, 9, 55.
49. Henry, R. A.; Dehn, W. M. J. Am. Chem. Soc. 1949, 71, 2297.