Introduction of heteroatom-based substituents into 1,4-dihydropyridines by means of a halogen-mediated, oxidative protocol: Diamination, sulfonylation, sulfinylation, bis-sulfanylation, and halo-phosphonylation processes

Chemistry - A European Journal

Volumn 6, Issue 10, 2000, Pages 1763-1772

  Lavilla, Rodolfo ^a   Kumar, Rakesh ^a   Coll, Oscar ^a   Masdeu, Carme ^a   Spada, Alessandro ^a   Bosch, Joan ^a   Espinosa, Enric ^b   Molins, Elies ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

Author keywords

Amination; Dihydropyridines; Heterocycles; Oxidations; Synthetic methods

Indexed keywords

HETEROCYCLIC AMINE; PYRIDINE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; OXIDATION; REACTION ANALYSIS;

EID: 0034660255     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000515)6:10<1763::aid-chem1763>3.0.co;2-r     Document Type: Article

References (78)

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3. For reviews on the chemistry of dihydropyridines, see: a) U. Eisner, J. Kuthan, Chem. Rev. 1972, 72, 1-42; b) D. M. Stout, A. I. Meyers, Chem. Rev. 1982, 82, 223-243; c) J. P. Kutney, Heterocycles 1977, 7, 593-614; d) D. L. Comins, S. O'Cannor, Adv. Heterocycl. Chem. 1988, 44, 199-267; e) S. Goldmann, J. Stoltefuss, Angew. Chem. 1991, 103, 1587-1606; Angew. Chem. Int. Ed. Engl. 1991, 30, 1559-1578.
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5. For reviews on the chemistry of dihydropyridines, see: a) U. Eisner, J. Kuthan, Chem. Rev. 1972, 72, 1-42; b) D. M. Stout, A. I. Meyers, Chem. Rev. 1982, 82, 223-243; c) J. P. Kutney, Heterocycles 1977, 7, 593-614; d) D. L. Comins, S. O'Cannor, Adv. Heterocycl. Chem. 1988, 44, 199-267; e) S. Goldmann, J. Stoltefuss, Angew. Chem. 1991, 103, 1587-1606; Angew. Chem. Int. Ed. Engl. 1991, 30, 1559-1578.
6. For reviews on the chemistry of dihydropyridines, see: a) U. Eisner, J. Kuthan, Chem. Rev. 1972, 72, 1-42; b) D. M. Stout, A. I. Meyers, Chem. Rev. 1982, 82, 223-243; c) J. P. Kutney, Heterocycles 1977, 7, 593-614; d) D. L. Comins, S. O'Cannor, Adv. Heterocycl. Chem. 1988, 44, 199-267; e) S. Goldmann, J. Stoltefuss, Angew. Chem. 1991, 103, 1587-1606; Angew. Chem. Int. Ed. Engl. 1991, 30, 1559-1578.
7. a) For pioneering studies in this field, see: E. Wenkert, Pure Appl. Chem. 1981, 53, 1271-1276;
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9. for reviews, see: b) M.-L. Bennasar, R. Lavilla, M. Alvarez, J. Bosch, Hetreocycles 1988, 27, 789-824; c) M.-L. Bennasar, J. Bosch. Synlett 1995, 587-596.
10. a) R. Lavilla, O. Coll, R. Kumar, J. Bosch, J. Org. Chem. 1998, 63, 2728-2730;
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15. K. Nishiyama in Encyclopaedia of Reagents for Organic Synthesis, Vol. 1 (Ed.: L. E. Paquette), Wiley, Chicnester, 1995, pp. 222-224.
16. a) For a recent account of the stereochemistry of this kind of reaction, see: G. Bellucci, C. Chiappe, F. D'Andrea, G. Lo Moro, Tetrahedron 1997, 53, 3417-3424;
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24. Among them: 2-hydroxy-3-iodotetrahydropyridines, 3-substituted 5-formyl-1-methylpyrroles, and tetrahydropyridine dimers. For the formation and characterization of these compounds, see ref. [3a].
25. For a general review of olefin amination reactions promoted by electrophiles, see: a) M. Orena in Methods of Organic Chemistry, Stereoselective Synthesis, Vol. 9 (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1996, pp. 5291-5355. Only intramolecular haloamination of olefins is relevant in synthesis, see inter alia: b) D. R. Williams, D. L. Brown, J. W. Benbow, J. Am. Chem. Soc. 1989, 111, 1923-1925; c) D. Tanner, M. Sellén, J. E. Bäckvall, J. Org. Chem. 1989, 54, 3374-3378; d) W. R. Bowman, D. L. Clark, R. J. Marmon, Tetrahedron 1994, 50, 1275-1294.
26. For a general review of olefin amination reactions promoted by electrophiles, see: a) M. Orena in Methods of Organic Chemistry, Stereoselective Synthesis, Vol. 9 (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1996, pp. 5291-5355. Only intramolecular haloamination of olefins is relevant in synthesis, see inter alia: b) D. R. Williams, D. L. Brown, J. W. Benbow, J. Am. Chem. Soc. 1989, 111, 1923-1925; c) D. Tanner, M. Sellén, J. E. Bäckvall, J. Org. Chem. 1989, 54, 3374-3378; d) W. R. Bowman, D. L. Clark, R. J. Marmon, Tetrahedron 1994, 50, 1275-1294.
27. For a general review of olefin amination reactions promoted by electrophiles, see: a) M. Orena in Methods of Organic Chemistry, Stereoselective Synthesis, Vol. 9 (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1996, pp. 5291-5355. Only intramolecular haloamination of olefins is relevant in synthesis, see inter alia: b) D. R. Williams, D. L. Brown, J. W. Benbow, J. Am. Chem. Soc. 1989, 111, 1923-1925; c) D. Tanner, M. Sellén, J. E. Bäckvall, J. Org. Chem. 1989, 54, 3374-3378; d) W. R. Bowman, D. L. Clark, R. J. Marmon, Tetrahedron 1994, 50, 1275-1294.
28. For a general review of olefin amination reactions promoted by electrophiles, see: a) M. Orena in Methods of Organic Chemistry, Stereoselective Synthesis, Vol. 9 (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1996, pp. 5291-5355. Only intramolecular haloamination of olefins is relevant in synthesis, see inter alia: b) D. R. Williams, D. L. Brown, J. W. Benbow, J. Am. Chem. Soc. 1989, 111, 1923-1925; c) D. Tanner, M. Sellén, J. E. Bäckvall, J. Org. Chem. 1989, 54, 3374-3378; d) W. R. Bowman, D. L. Clark, R. J. Marmon, Tetrahedron 1994, 50, 1275-1294.
29. For a preliminary account of part of this section, see: R. Lavilla, R. Kumar, O. Coll, C. Masdeu, J. Bosch, Chem. Commun. 1998, 2715-2716.
30. For a related regio- and stereoselective ring opening of aziridinium ions, see: S. E. de Sousa, P. O'Brien, Tetrahedron Lett. 1997, 38, 4885-4888.
31. For an efficient two-step synthesis of structurally related cis-vicinal diamines from electron-rich alkenes, see: a) G. Fraenkel, J. Galluci, H. S. Rosenzweig, J. Org. Chem. 1989, 54, 677-681; b) J. Akester, J. Cui, G. Fraenkel, J. Org. Chem. 1997, 62, 431-434.
32. For an efficient two-step synthesis of structurally related cis-vicinal diamines from electron-rich alkenes, see: a) G. Fraenkel, J. Galluci, H. S. Rosenzweig, J. Org. Chem. 1989, 54, 677-681; b) J. Akester, J. Cui, G. Fraenkel, J. Org. Chem. 1997, 62, 431-434.
33. For the preparation of 1,2-diamines from alkenes, see: D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627 and references therein.
34. For the preparation of 1,2-diamines from alkenes, see: D. Lucet, T. Le Gall, C. Mioskowski, Angew. Chem. 1998, 110, 2724-2772; Angew. Chem. Int. Ed. 1998, 37, 2580-2627 and references therein.
35. In this experiment the unreacted dihydropyridine 1b was recovered in 60% yield. This indicates an unexpected robustness for these compounds which were previously considered to be labile.
36. For a recent and effective method to carry out this transformation, see: J. Du Bois, C. S. Tomooka, J. Hong, E. M. Carreira, J. Am. Chem. Soc. 1997, 119, 3179-3180.
37. E. J. Corey, S. Sarshar, M. D. Azimioara, R. C. Newbold, M. C. Noe, J. Am. Chem. Soc. 1996, 118, 7851-7852.
38. For some recent references on the solution-phase combinatorial synthesis, see: a) D. L. Boger, C. M. Tarby, P. L. Myers, L. H. Caporale, J. Am. Chem. Soc. 1996, 118, 2109-2110; b) L. Neuville, J. Zhu, Tetrahedron Lett. 1997, 38, 4091-4094, and references therein: c) D. L. Boger, J. Goldberg, C.-M. Andersson, J. Org. Chem. 1999, 64, 2422-2427.
39. For some recent references on the solution-phase combinatorial synthesis, see: a) D. L. Boger, C. M. Tarby, P. L. Myers, L. H. Caporale, J. Am. Chem. Soc. 1996, 118, 2109-2110; b) L. Neuville, J. Zhu, Tetrahedron Lett. 1997, 38, 4091-4094, and references therein: c) D. L. Boger, J. Goldberg, C.-M. Andersson, J. Org. Chem. 1999, 64, 2422-2427.
40. For some recent references on the solution-phase combinatorial synthesis, see: a) D. L. Boger, C. M. Tarby, P. L. Myers, L. H. Caporale, J. Am. Chem. Soc. 1996, 118, 2109-2110; b) L. Neuville, J. Zhu, Tetrahedron Lett. 1997, 38, 4091-4094, and references therein: c) D. L. Boger, J. Goldberg, C.-M. Andersson, J. Org. Chem. 1999, 64, 2422-2427.
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43. For recent work on this subject, see: a) J. U. Jeong, B. Tao, I. Sagasser, H. Henniges, K. B. Sharpless, J. Am. Chem. Soc. 1998, 120, 6844-6845; b) T. Ando, D. Kano, S. Minakata, I. Ryu, M. Komatsu, Tetrahedron 1998, 54, 13485-13494; c) S. Minakata, T. Ando, M. Nishimura, I. Ryu, M. Komatsu, Angew. Chem. 1998, 110, 3596-3598; Angew. Chem. Int. Ed. 1998, 37, 3392-3394; d) M. Sunose, K. M. Anderson, G. Orpen, T. Gallagher, S. F. Macdonald, Tetrahedron Lett. 1998, 39, 8885-8888; e) See also ref. [18].
44. For recent work on this subject, see: a) J. U. Jeong, B. Tao, I. Sagasser, H. Henniges, K. B. Sharpless, J. Am. Chem. Soc. 1998, 120, 6844-6845; b) T. Ando, D. Kano, S. Minakata, I. Ryu, M. Komatsu, Tetrahedron 1998, 54, 13485-13494; c) S. Minakata, T. Ando, M. Nishimura, I. Ryu, M. Komatsu, Angew. Chem. 1998, 110, 3596-3598; Angew. Chem. Int. Ed. 1998, 37, 3392-3394; d) M. Sunose, K. M. Anderson, G. Orpen, T. Gallagher, S. F. Macdonald, Tetrahedron Lett. 1998, 39, 8885-8888; e) See also ref. [18].
45. For recent work on this subject, see: a) J. U. Jeong, B. Tao, I. Sagasser, H. Henniges, K. B. Sharpless, J. Am. Chem. Soc. 1998, 120, 6844-6845; b) T. Ando, D. Kano, S. Minakata, I. Ryu, M. Komatsu, Tetrahedron 1998, 54, 13485-13494; c) S. Minakata, T. Ando, M. Nishimura, I. Ryu, M. Komatsu, Angew. Chem. 1998, 110, 3596-3598; Angew. Chem. Int. Ed. 1998, 37, 3392-3394; d) M. Sunose, K. M. Anderson, G. Orpen, T. Gallagher, S. F. Macdonald, Tetrahedron Lett. 1998, 39, 8885-8888; e) See also ref. [18].
46. For recent work on this subject, see: a) J. U. Jeong, B. Tao, I. Sagasser, H. Henniges, K. B. Sharpless, J. Am. Chem. Soc. 1998, 120, 6844-6845; b) T. Ando, D. Kano, S. Minakata, I. Ryu, M. Komatsu, Tetrahedron 1998, 54, 13485-13494; c) S. Minakata, T. Ando, M. Nishimura, I. Ryu, M. Komatsu, Angew. Chem. 1998, 110, 3596-3598; Angew. Chem. Int. Ed. 1998, 37, 3392-3394; d) M. Sunose, K. M. Anderson, G. Orpen, T. Gallagher, S. F. Macdonald, Tetrahedron Lett. 1998, 39, 8885-8888; e) See also ref. [18].
47. For recent work on this subject, see: a) J. U. Jeong, B. Tao, I. Sagasser, H. Henniges, K. B. Sharpless, J. Am. Chem. Soc. 1998, 120, 6844-6845; b) T. Ando, D. Kano, S. Minakata, I. Ryu, M. Komatsu, Tetrahedron 1998, 54, 13485-13494; c) S. Minakata, T. Ando, M. Nishimura, I. Ryu, M. Komatsu, Angew. Chem. 1998, 110, 3596-3598; Angew. Chem. Int. Ed. 1998, 37, 3392-3394; d) M. Sunose, K. M. Anderson, G. Orpen, T. Gallagher, S. F. Macdonald, Tetrahedron Lett. 1998, 39, 8885-8888; e) See also ref. [18].
48. For recent work on this subject, see: a) J. U. Jeong, B. Tao, I. Sagasser, H. Henniges, K. B. Sharpless, J. Am. Chem. Soc. 1998, 120, 6844-6845; b) T. Ando, D. Kano, S. Minakata, I. Ryu, M. Komatsu, Tetrahedron 1998, 54, 13485-13494; c) S. Minakata, T. Ando, M. Nishimura, I. Ryu, M. Komatsu, Angew. Chem. 1998, 110, 3596-3598; Angew. Chem. Int. Ed. 1998, 37, 3392-3394; d) M. Sunose, K. M. Anderson, G. Orpen, T. Gallagher, S. F. Macdonald, Tetrahedron Lett. 1998, 39, 8885-8888; e) See also ref. [18].
49. a) For a Hantzsch-type synthesis of a 3-sulfonyl-1,4-dihydropyridine, see: R. Davis, J. R. Kern, L. J. Kurz, J. R. Pfister, J. Am. Chem. Soc. 1988, 110, 7873-7874;
50. b) For the recent synthesis of diversely substituted 5-sulfonyl-1,2,3,4-tetrahydropyridines, see: Y. Horino, M. Kimura, Y. Wakamiya, T. Okajima, Y. Tamaru, Angew. Chem. 1999, 111, 123-1246; Angew. Chem. Int. Ed. 1999, 38, 121-124.
51. b) For the recent synthesis of diversely substituted 5-sulfonyl-1,2,3,4-tetrahydropyridines, see: Y. Horino, M. Kimura, Y. Wakamiya, T. Okajima, Y. Tamaru, Angew. Chem. 1999, 111, 123-1246; Angew. Chem. Int. Ed. 1999, 38, 121-124.
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56. Similar results were observed with methyl 1-(3-methyl-3-butenyl)-1,4-dihydropyridine-3-carboxylate. The corresponding sulfonyldihydropyridine was obtained as the major product, although it was not purified.
57. N. S. Simpkins, Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993, Chapters 4, 6, and 9.
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59. For a process which may be consistent with this hypothesis, see: P. Stanetty, M. D. Mihovilovic, K. Mereiter, Monatsch. Chem. 1997, 128, 1061-1072.
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65. It has been claimed that a "dithiocyano adduct" was obtained through interaction of 1,4-dihydropyridines with thiocyanogen (H. P. Kaufmann, J. Liepe, Ber. 1923, 56, 2514-2520); however, "the structure has not been established" (also see comments on ref. [1a]).
66. For a report of an halosulfanylation of a NADH analogue, see: K. Wallenfels, D. Hofmann, H. Schüly, Liebigs Ann. Chem. 1959, 621, 188-197.
67. For alternative bis-sulfanylation strategies that take place with alkenes, see: a) M. C. Caserio, C. L. Fisher, J. K. Kim, J. Org. Chem. 1985, 50, 4390-4393; b) T. Kondo, S. Uenoyama, K. Fujita, T. Mitsudo, J. Am. Chem. Soc. 1999, 121, 482-483.
68. For alternative bis-sulfanylation strategies that take place with alkenes, see: a) M. C. Caserio, C. L. Fisher, J. K. Kim, J. Org. Chem. 1985, 50, 4390-4393; b) T. Kondo, S. Uenoyama, K. Fujita, T. Mitsudo, J. Am. Chem. Soc. 1999, 121, 482-483.
69. For early reports on the halogenation of 1,4-dihydropyridines that lead to heptachloro and tetrabromo compounds "whose structures were not established" (comments on ref. [1a]), see: a) A. Hantzsch, Justus Liebigs Ann. Chem. 1882, 215, 1-13; b) E. Benary, Chem. Ber. 1918, 51, 567-577; c) for the bromination of the more stable N-acyldihydropyridines, see: J. Urbanski, L. Wrobel, Pol. J. Chem. 1986, 59, 1099-1106.
70. For early reports on the halogenation of 1,4-dihydropyridines that lead to heptachloro and tetrabromo compounds "whose structures were not established" (comments on ref. [1a]), see: a) A. Hantzsch, Justus Liebigs Ann. Chem. 1882, 215, 1-13; b) E. Benary, Chem. Ber. 1918, 51, 567-577; c) for the bromination of the more stable N-acyldihydropyridines, see: J. Urbanski, L. Wrobel, Pol. J. Chem. 1986, 59, 1099-1106.
71. For early reports on the halogenation of 1,4-dihydropyridines that lead to heptachloro and tetrabromo compounds "whose structures were not established" (comments on ref. [1a]), see: a) A. Hantzsch, Justus Liebigs Ann. Chem. 1882, 215, 1-13; b) E. Benary, Chem. Ber. 1918, 51, 567-577; c) for the bromination of the more stable N-acyldihydropyridines, see: J. Urbanski, L. Wrobel, Pol. J. Chem. 1986, 59, 1099-1106.
72. It should be noted that the halogen interaction with dihydropyridines is reported in several reviews (ref. [1a]) as an efficient procedure for the "biomimetic" oxidation of these compounds, leading to the corresponding pyridinium salts, and it has even been proposed as an analytical method for the estimation of the dihydropyridine content. Our results, however, are in good agreement with our recently described alkoxyhalogenation processes (see ref. [3a]). In sharp contrast, a related 1,2,3,4-tetrahydropyridine under similar reaction conditions afforded the bromoiminium bromide: D. Donati, S. Fusi, M. A. Macripò, F. Ponticelli, J. Heterocyclic Chem. 1987, 24, 481-483.
73. For a discussion of the role of the solvent on the stereochemical course of halogen additions to alkenes, see: C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 2nd ed., VCH, Weinheim, 1988, pp. 248-249, and references therein.
74. Interestingly, when lithium diethylphosphite was added to a solution containing dibromide 17, a clean dehalogenation took place, and dihydropyridine 1b was obtained in nearly quantitative yield.
75. For recent examples of phosphonates linked to 6-membered nitrogen heterocycles, see: a) A. R. Katritzky, G. Qiu, B. Yang, P. J. Steel, J. Org. Chem. 1998, 63, 6699-6703; b) D. Albouy, M. Laspéras, G. Etemad-Moghadam, M. Koenig, Tetrahedron Lett. 1999, 40, 2311-2314.
76. For recent examples of phosphonates linked to 6-membered nitrogen heterocycles, see: a) A. R. Katritzky, G. Qiu, B. Yang, P. J. Steel, J. Org. Chem. 1998, 63, 6699-6703; b) D. Albouy, M. Laspéras, G. Etemad-Moghadam, M. Koenig, Tetrahedron Lett. 1999, 40, 2311-2314.
77. a) M. E. Brewster, A. Simay, K. Czako, D. Winwood, H. Farag, N. Bodor, J. Org. Chem. 1989, 54, 3721-3726;
78. b) Dihydropyridine 1h was prepared following a published procedure: M. Lounasmaa, C.-J. Johansson, Tetrahedron 1977, 33, 113-117.