Synthesis of stable 1H-azirines reinvestigated: A structural corrigendum

Synlett

Volumn 23, Issue 20, 2012, Pages 2943-2946

  Banert, Klaus ^a   Hagedorn, Manfred ^a   Peisker, Heiko ^a  

^a CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

acylation; antiaromatic heterocycles; assignment by spectroscopy; structure; ureas

Indexed keywords

1H AZIRINE DERIVATIVE; AZIRINE DERIVATIVE; ISOQUINOLINE; N ACYL N,N' DIALKYLUREA; N,N' DIALKYLCARBODIIMIDE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 84868496361     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1317494     Document Type: Article

References (58)

1. Backes J. In Houben-Weyl. Vol. E16c nd; Klamann D. Thieme Stuttgart: 1992; 321
2. Nair V. In The Chemistry of Heterocyclic Compounds, Small-Ring Heterocycles. Vol. 42, Part 1 Hassner A. Wiley New York: 1983; 215
3. Pearson W. H., Lian B. W., Bergmeier S. C. In Comprehensive Heterocyclic Chemistry II. Vol. 1A Padwa A. Pergamon New York: 1996; 1
4. Palacios F., Ochoa de Retana A. N., Martinez de Marigorta E., de Los Santos J. M. Eur. J. Org. Chem.: 2001; 2401
5. Gilchrist T. L. Aldrichimica Acta: 2001; 34 51
6. Rai K. M. L, Hassner A. In Advances in Strained and Interesting Organic Molecules. Vol. 8 Halton B. Jai Press Greenwich: 2000; 187
7. Fowler F. W. Adv. Heterocycl. Chem.: 1971; 13 45
8. Wentrup C. Adv. Heterocycl. Chem.: 1981; 28 231
9. Miller T. W., Tristram E. W., Wolf F. J. J. Antibiot.: 1971; 24 48
10. Molinski T. F., Ireland C. M. J. Org. Chem.: 1988; 53 2103
11. Salomon C. E., Williams D. H., Faulkner D. J. J. Nat. Prod.: 1995; 58 1463
12. Stapley E. O., Hendlin D., Jackson M., Miller A. K., Hernandez S., Mata J. M. J. Antibiot.: 1971; 24 42
13. Davis F. A., Reddy G. V., Liu H. J. Am. Chem. Soc.: 1995; 117 3651
14. Davis F. A., Liu H., Liang C.-H, Reddy G. V., Zhang Y., Fang T., Titus D. D. J. Org. Chem.: 1999; 64 8929
15. Jacox M. E., Milligan D. E. J. Am. Chem. Soc.: 1963; 85 278
16. Kodama S. J. Phys. Chem.: 1988; 92 5019
17. Fowler F. W., Hassner A. J. Am. Chem. Soc.: 1968; 90 2875
18. Anderson D. J., Gilchrist T. L., Rees C. W. Chem. Commun.: 1969; 147
19. Gilchrist T. L., Gymer G. E., Rees C. W. Chem. Commun.: 1971; 1519
20. Anderson D. J., Gilchrist T. L., Gymer G. E., Rees C. W. J. Chem. Soc., Perkin Trans. 1: 1973; 550
21. Gilchrist T. L., Gymer G. E., Rees C. W. J. Chem. Soc., Perkin Trans. 1: 1973; 555
22. Atkinson R. S., Grimshire M. J. J. Chem. Soc., Perkin Trans. 1: 1986; 1215
23. Mitchell G., Rees C. W. J. Chem. Soc., Chem. Commun.: 1986; 399
24. Mitchell G., Rees C. W. J. Chem. Soc., Perkin Trans. 1: 1987; 413
25. Huisgen R., Blaschke H. Chem. Ber.: 1965; 98 2985
26. Meinwald J., Aue D. H. J. Am. Chem. Soc.: 1966; 88 2849
27. Wentrup C., Crow W. D. Tetrahedron: 1970; 26 3965
28. Thétaz C., Wentrup C. J. Am. Chem. Soc.: 1976; 98 1258
29. Clark D. T. Theoret. Chim. Acta (Berl.): 1969; 15 225
30. Hopkinson A. C., Lien M. H., Yates K., Csizmadia I. G. Int. J. Quantum Chem.: 1977; 12 355
31. Bock H., Dammel R. Chem. Ber.: 1987; 120 1971
32. Alcami M., Mó O., Yáñez M. J. Am. Chem. Soc.: 1993; 115 11074
33. Lathan W. A., Radom L., Hariharan P. C., Hehre W. J., Pople J. A. Top. Curr. Chem.: 1973; 40 1
34. Mó O., Yáñez M., Elguero J. J. Mol. Struct. (Theochem): 1989; 201 17
35. Byun Y.-G, Saebo S., Pittman C. U. J. Am. Chem. Soc.: 1991; 113 3689
36. Malar E. J. P. Tetrahedron: 1996; 52 4709
37. Budzelaar P. H. M, Cremer D., Wallasch M., Würthwein E.-U, Schleyer P.v.R. J. Am. Chem. Soc.: 1987; 109 6290
38. Alcami M., de Paz J. L. G, Yáñez M. J. Comp. Chem.: 1989; 10 468
39. Würthwein E.-U. J. Org. Chem.: 1984; 49 2971
40. Mó O., de Paz J. L. G, Yáñez M. J. Phys. Chem.: 1987; 91 6484
41. Lessene G., Smith B. J., Gable R. W., Baell J. B. J. Org. Chem.: 2009; 74 6511
42. Corriu R. J. P, Lanneau G. F., Perrot-Petta M. Synthesis: 1991; 954
43. Neves Filho R. A. W, de Oliveira R. N., Srivastava R. M. J. Braz. Chem. Soc.: 2007; 18 1410
44. Quintanilla M. G., Montero G., Hierro A. G., Diaz J. M., Bassani S. Acta Chem. Scand.: 1999; 53 928
45. Kishikawa K., Eida H., Kohmoto S., Yamamoto M., Yamada K. Synthesis: 1994; 173
46. Bamberger E. Ber. Dtsch. Chem. Ges.: 1887; 20 3338
47. Schmidt E., van Ark H. H. Arch. Pharm.: 1900; 238 321
48. Babcock S. H., Nakamura F. I., Fuson R. C. J. Am. Chem. Soc.: 1932; 54 4407
49. Krollpfeiffer F., Müller A. Ber. Dtsch. Chem. Ges. B: 1933; 66 739
50. Babcock S. H., Fuson R. C. J. Am. Chem. Soc.: 1933; 55 2946
51. Kröhnke F., Heffe W. Ber. Dtsch. Chem. Ges. B: 1937; 70 864
52. Pearson R. G., Dillon R. L. J. Am. Chem. Soc.: 1948; 70 1933
53. Pearson R. G., Sandy A. C. J. Am. Chem. Soc.: 1951; 73 931
54. King L. C. J. Am. Chem. Soc.: 1944; 66 894
55. King L. C. J. Am. Chem. Soc.: 1944; 66 1612
56. King L. C., McWhirter M., Rowland R. L. J. Am. Chem. Soc.: 1948; 70 239
57. Huffman J. W., Zengin G., Wu M.-J, Lu J., Hynd G., Bushell K., Thompson A. L. S, Bushell S., Tartal C., Hurst D. P., Reggio P. H., Selley D. E., Cassidy M. P., Wiley J. L., Martin B. R. Bioorg. Med. Chem.: 2005; 13 89
58. Brusotti G., Habermann J., Azzolina O., Collina S. Lett. Org. Chem.: 2006; 3 943