Synthesis with perfect atom economy: Generation of diazo ketones by 1,3-dipolar cycloaddition of nitrous oxide at cyclic alkynes under mild conditions

Angewandte Chemie - International Edition

Volumn 50, Issue 27, 2011, Pages 6171-6174

  Banert, Klaus ^a   Plefka, Oliver ^a  

^a CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

cascade reactions; nitrogen heterocycles; reaction mechanisms; rearrangements; strained compounds

Indexed keywords

CASCADE REACTIONS; NITROGEN HETEROCYCLES; REACTION MECHANISM; REARRANGEMENTS; STRAINED COMPOUNDS;

ACETYLENE; ANESTHETICS; CYCLOADDITION; KETONES; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

NITROGEN OXIDES;

ALKYNE; AZO COMPOUND; KETONE; NITROUS OXIDE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; AZO COMPOUNDS; CYCLIZATION; KETONES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NITROUS OXIDE;

EID: 79959527516     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101326     Document Type: Article

References (77)

1. Review:, A. V. Leont'ev, O. A. Fomicheva, M. V. Proskurnina, N. S. Zefirov, Russ. Chem. Rev. 2001, 70, 91-104, and references therein.
2. J. Ettedgui, R. Neumann, J. Am. Chem. Soc. 2009, 131, 4-5
3. H. Matsumoto, S. Tanabe, K. Okitsu, Y. Hayashi, S. L. Suib, J. Phys. Chem. A 2001, 105, 5304-5308
4. P. Kuśtrowski, L. Chmielarz, R. Dziembaj, P. Cool, E. F. Vansant, J. Phys. Chem. A 2005, 109, 330-336
5. S. Poh, R. Hernandez, M. Inagaki, P. G. Jessop, Org. Lett. 1999, 1, 583-585
6. F. Rondinelli, N. Russo, M. Toscano, Inorg. Chem. 2007, 46, 7489-7493
7. F. Rondinelli, N. Russo, M. Toscano, J. Chem. Theory Comput. 2008, 4, 1886-1890
8. K. Pacultová, L. Obalová, F. Kovanda, K. Jirátová, Catal. Today 2008, 137, 385-389
9. J. R. Bleeke, R. Behm, Y.-F. Xie, T. W. Clayton, Jr., K. D. Robinson, J. Am. Chem. Soc. 1994, 116, 4093-4094
10. N. D. Harrold, R. Waterman, G. L. Hillhouse, T. R. Cundari, J. Am. Chem. Soc. 2009, 131, 12872-12873.
11. G. I. Panov, A. S. Kharitonov, V. I. Sobolev, Appl. Catal. A 1993, 98, 1-20
12. V. I. Sobolev, A. S. Kharitonov, Ye. A. Paukshtis, G. I. Panov, J. Mol. Catal. 1993, 84, 117-124
13. G. I. Panov, A. K. Uriarte, M. A. Rodkin, V. I. Sobolev, Catal. Today 1998, 41, 365-385
14. H. Xin, A. Koekkoek, Q. Yang, R. vanSanten, C. Li, E. J. M. Hensen, Chem. Commun. 2009, 7590-7592.
15. R. Ben-Daniel, L. Weiner, R. Neumann, J. Am. Chem. Soc. 2002, 124, 8788-8789
16. T. Thömmes, I. Gräf, A. Reitzmann, B. Kraushaar-Czarnetzki, Ind. Eng. Chem. Res. 2010, 49, 2624-2637
17. X. Wang, Q. Zhang, S. Yang, Y. Wang, J. Phys. Chem. B 2005, 109, 23500-23508
18. T. Yamada, K. Hashimoto, Y. Kitaichi, K. Suzuki, T. Ikeno, Chem. Lett. 2001, 268-269
19. H. Tanaka, K. Hashimoto, K. Suzuki, Y. Kitaichi, M. Sato, T. Ikeno, T. Yamada, Bull. Chem. Soc. Jpn. 2004, 77, 1905-1914
20. E. K. Beloglazkina, A. G. Majouga, A. A. Moiseeva, N. V. Zyk, N. S. Zefirov, Mendeleev Commun. 2009, 19, 69-71.
21. F. S. Bridson-Jones, G. D. Buckley, L. H. Cross, A. P. Driver, J. Chem. Soc. 1951, 2999-3008
22. G. I. Panov, K. A. Dubkov, E. V. Starokon, V. N. Parmon, React. Kinet. Catal. Lett. 2002, 76, 401-406.
23. K. A. Dubkov, G. I. Panov, E. V. Starokon, V. N. Parmon, React. Kinet. Catal. Lett. 2002, 77, 197-205.
24. F. S. Bridson-Jones, G. D. Buckley, J. Chem. Soc. 1951, 3009-3016
25. E. V. Starokon, K. A. Dubkov, D. E. Babushkin, V. N. Parmon, G. I. Panov, Adv. Synth. Catal. 2004, 346, 268-274
26. E. V. Starokon, K. A. Dubkov, V. N. Parmon, G. I. Panov, React. Kinet. Catal. Lett. 2005, 84, 383-388
27. S. V. Semikolenov, K. A. Dubkov, E. V. Starokon, D. E. Babushkin, G. I. Panov, Russ. Chem. Bull. Int. Ed. 2005, 54, 948-956
28. I. Hermans, B. Moens, J. Peeters, P. Jacobs, B. Sels, Phys. Chem. Chem. Phys. 2007, 9, 4269-4274.
29. For the equilibrium of α-diazo carbonyl compounds and 1,2,3-oxadiazoles, see M. T. Nguyen, A. F. Hegarty, J. Elguero, Angew. Chem. 1985, 97, 704-705
30. Angew. Chem. Int. Ed. Engl. 1985, 24, 713-715
31. W. M. F. Fabian, V. A. Bakulev, C. O. Kappe, J. Org. Chem. 1998, 63, 5801-5805
32. R. Schulz, A. Schweig, Angew. Chem. 1984, 96, 494-495
33. Angew. Chem. Int. Ed. Engl. 1984, 23, 509-511
34. A. Blocher, K.-P. Zeller, Angew. Chem. 1991, 103, 1489-1490
35. Angew. Chem. Int. Ed. Engl. 1991, 30, 1476-1477.
36. G. D. Buckley, W. J. Levy, J. Chem. Soc. 1951, 3016-3018.
37. R. Huisgen, Angew. Chem. 1963, 75, 604-637
38. Angew. Chem. Int. Ed. Engl. 1963, 2, 565-598.
39. V. I. Avdeev, S. P. Ruzankin, G. M. Zhidomirov, Chem. Commun. 2003, 42-43
40. K. N. Houk, J. Sims, C. R. Watts, L. J. Luskus, J. Am. Chem. Soc. 1973, 95, 7301-7315
41. M.-D. Su, H.-Y. Liao, W.-S. Chung, S.-Y. Chu, J. Org. Chem. 1999, 64, 6710-6716
42. K. N. Houk, J. Am. Chem. Soc. 1972, 94, 8953-8955
43. D. H. Ess, K. N. Houk, J. Phys. Chem. A 2005, 109, 9542-9553
44. S. Grimme, C. Mück-Lichtenfeld, E.-U. Würthwein, A. W. Ehlers, T. P. M. Goumans, K. Lammertsma, J. Phys. Chem. A 2006, 110, 2583-2586
45. D. H. Ess, K. N. Houk, J. Am. Chem. Soc. 2008, 130, 10187-10198
46. L. T. Nguyen, F. DeProft, V. L. Dao, M. T. Nguyen, P. Geerlings, J. Phys. Org. Chem. 2003, 16, 615-625
47. L. T. Nguyen, F. DeProft, A. K. Chandra, T. Uchimaru, M. T. Nguyen, P. Geerlings, J. Org. Chem. 2001, 66, 6096-6103
48. B. Braida, C. Walter, B. Engels, P. C. Hiberty, J. Am. Chem. Soc. 2010, 132, 7631-7637.
49. For the synthesis of 12 without using 10 or 11, see M. A. Davis, F. Herr, R. A. Thomas, M.-P. Charest, J. Med. Chem. 1967, 10, 627-635
50. J. Platzek, G. Snatzke, Tetrahedron 1987, 43, 4947-4968.
51. H. Meier, H. Gugel, Synthesis 1976, 338-339
52. C. S. McKay, J. Moran, J. P. Pezacki, Chem. Commun. 2010, 46, 931-933.
53. A bottle with nitrous oxide for medical use (50bar, ca. 0.21Euro per mole) was utilized. R. L. Danheiser, A. L. Helgason, J. Am. Chem. Soc. 1994, 116, 9471-9479
54. H. Tomioka, A. Okuno, T. Sugiyama, S. Murata, J. Org. Chem. 1995, 60, 2344-2352
55. W. Kirmse, Eur. J. Org. Chem. 2002, 2193-2256.
56. A. Krebs, H. Kimling, Tetrahedron Lett. 1970, 11, 761-764
57. A. Krebs, H. Kimling, Justus Liebigs Ann. Chem. 1974, 2074-2084.
58. A. deGroot, J. A. Boerma, J. deValk, H. Wynberg, J. Org. Chem. 1968, 33, 4025-4029.
59. For details, see the Supporting Information. V. V. Popik, V. A. Nikolaev, J. Chem. Soc. Perkin Trans. 2 1993, 1791-1793.
60. L. F. Tietze, T. Eicher, Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium, 2 nd ed., Thieme, Stuttgart, 1991, p. 40.
61. H. Petersen, H. Meier, Chem. Ber. 1980, 113, 2383-2397
62. M. Schmitt, Dissertation, Universität Mainz, 1992.
63. For the thermal decomposition of 20 a, see:, P. W. Concannon, J. Ciabattoni, J. Am. Chem. Soc. 1973, 95, 3284-3289.
64. Clearly, diazo ketone 20, generated from 18 and nitrous oxide, added 18 very rapidly so that the Wolff rearrangement of 20 could not compete. On the other hand, attempts to trap the intermediate 20 by electron-deficient alkynes, such as dimethyl acetylenedicarboxylate (see Ref.[24]) or dicyanoacetylene (to avoid addition of 18) were unsuccessful.
65. For similar rearrangement reactions of 3-acyl-3H-pyrazoles to produce 1-acyl-1H-pyrazoles, see:, M. Martin, M. Regitz, Justus Liebigs Ann. Chem. 1974, 1702-1708.
66. R. F. Smith, F. K. Kirchner, J. Org. Chem. 1958, 23, 621
67. A. L. Johnson, P. B. Sweetser, J. Org. Chem. 1976, 41, 110-114
68. J. Bermudez, C. S. Fake, G. F. Joiner, K. A. Joiner, F. D. King, W. D. Miner, G. J. Sanger, J. Med. Chem. 1990, 33, 1924-1929
69. P. G. Baraldi, L. Garuti, M. Roberti, Synthesis 1994, 1437-1440
70. H. Harada, T. Morie, Y. Hirokawa, S. Kato, Chem. Pharm. Bull. 1996, 44, 2205-2212
71. P. G. Baraldi, B. Cacciari, R. Romagnoli, G. Spalluto, Synthesis 1999, 453-458.
72. M. Regitz, F. Menz, J. Rüter, Tetrahedron Lett. 1967, 8, 739-742
73. M. Regitz, J. Rüter, Chem. Ber. 1968, 101, 1263-1270.
74. C. B. Reese, A. Shaw, J. Chem. Soc. Chem. Commun. 1970, 1172-1173
75. T. Gerres, A. Heesing, Chem. Ber. 1992, 125, 1431-1437.
76. We prepared 23 a from 3-methoxycyclooctene by addition of bromine and subsequent treatment with potassium tert-butoxide and then treatment with lithium diisopropylamide, see the Supporting Information.
77. The unknown 23 b was synthesized from 3-bromocyclooctene by addition of bromine and subsequent treatment with potassium tert-butoxide. The resulting dibromides were treated with isopropylmagnesium bromide and then with lithium diisopropylamide, see the Supporting Information.