메뉴 건너뛰기




Volumn , Issue 23, 2009, Pages 3940-3952

Syntheses and15N NMR Spectra of Iminodiaziridines - Ring-Expansions of 1-Aryl-3-iminodiaziridines to 1H- and 3aH-Benzimidazoles, 2H-Indazoles, and 5H-Dibenzo[d,f] [1,3]diazepines

Author keywords

Diaziridines; Elimination; Guanidines; Nitrogen heterocycles; Sigmatropic rearrangement

Indexed keywords


EID: 68049117353     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900350     Document Type: Article
Times cited : (18)

References (103)
  • 1
    • 1342295971 scopus 로고
    • Reviews: a
    • Reviews: a) G. L'abbé, Angew. Chem. 1980, 92, 277-290;
    • (1980) Angew. Chem , vol.92 , pp. 277-290
    • L'abbé, G.1
  • 3
    • 68049131078 scopus 로고    scopus 로고
    • G. L'abbé, in Lectures in Heterocyclic Chemistry, 9 (Eds.: R. N. Castle, R. Neidlein), J. Heterocycl. Chem. 1987, 24 (Suppl.), pp. S-51S-58;
    • b) G. L'abbé, in Lectures in Heterocyclic Chemistry, vol. 9 (Eds.: R. N. Castle, R. Neidlein), J. Heterocycl. Chem. 1987, 24 (Suppl.), pp. S-51S-58;
  • 4
    • 68049131080 scopus 로고    scopus 로고
    • T. H. Chan, B. S. Ong, Tetrahedron 1980, 36, 22692289;
    • T. H. Chan, B. S. Ong, Tetrahedron 1980, 36, 22692289;
  • 7
    • 68049135585 scopus 로고    scopus 로고
    • f H. W. Heine, in The Chemistry of Heterocyclic Compounds, 42 (Small Ring Heterocycles) (Ed.: A. Hassner), Wiley, Chichester, UK, 1983, part 2, pp. 616-628;
    • f) H. W. Heine, in The Chemistry of Heterocyclic Compounds, vol. 42 (Small Ring Heterocycles) (Ed.: A. Hassner), Wiley, Chichester, UK, 1983, part 2, pp. 616-628;
  • 9
    • 68049116780 scopus 로고    scopus 로고
    • 2005, pp. 591-608.
    • 2005, pp. 591-608.
  • 10
    • 68049139119 scopus 로고    scopus 로고
    • H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075; Angew. Chem. Int. Ed. 2001, 40, 20042021;
    • a) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075; Angew. Chem. Int. Ed. 2001, 40, 20042021;
  • 15
  • 16
    • 0001389728 scopus 로고    scopus 로고
    • E.J. Corey, K. Ritter, M. Yus, C. Najera, Tetrahedron Lett. 1987, 28, 35473550;
    • b) E.J. Corey, K. Ritter, M. Yus, C. Najera, Tetrahedron Lett. 1987, 28, 35473550;
  • 17
    • 68049148213 scopus 로고    scopus 로고
    • J. K. Crandall, E. Rambo, Tetrahedron 2002, 58, 70277036.
    • J. K. Crandall, E. Rambo, Tetrahedron 2002, 58, 70277036.
  • 19
    • 33847675351 scopus 로고    scopus 로고
    • H. Quast, S. Aldenkortt, B. Freudenreich, P. Schäfer, M. Hagedorn, J. Lehmann, K. Banert, J. Org. Chem. 2007, 72, 16591666.
    • H. Quast, S. Aldenkortt, B. Freudenreich, P. Schäfer, M. Hagedorn, J. Lehmann, K. Banert, J. Org. Chem. 2007, 72, 16591666.
  • 20
    • 68049132736 scopus 로고    scopus 로고
    • H. Quast, E. Spiegel, Angew. Chem. 1977, 89, 112-113; Angew. Chem. Int. Ed. Engl. 1977, 16, 109-110;
    • a) H. Quast, E. Spiegel, Angew. Chem. 1977, 89, 112-113; Angew. Chem. Int. Ed. Engl. 1977, 16, 109-110;
  • 42
    • 68049135584 scopus 로고    scopus 로고
    • J. E. Bertie, M, G. Norton, Can. J. Chem. 1970, 48, 3889-3902;
    • b) J. E. Bertie, M, G. Norton, Can. J. Chem. 1970, 48, 3889-3902;
  • 44
    • 68049124645 scopus 로고    scopus 로고
    • G. J. Karabatsos, S. S. Lande, Tetrahedron 1968, 24, 39073922;
    • a) G. J. Karabatsos, S. S. Lande, Tetrahedron 1968, 24, 39073922;
  • 49
    • 68049120043 scopus 로고    scopus 로고
    • Ring-opening isomerizations of three-membered rings with exocyclic double bonds have been observed;a aziridinones: I. Lengyel, J. C. Sheehan, Angew. Chem. 1968, 80, 27-37;
    • Ring-opening isomerizations of three-membered rings with exocyclic double bonds have been observed;a) aziridinones: I. Lengyel, J. C. Sheehan, Angew. Chem. 1968, 80, 27-37;
  • 52
    • 0009471010 scopus 로고    scopus 로고
    • protonated iminoaziridines: H. Quast, S. Aldenkortt, B. Freudenreich, P. Schäfer, E.-M. Peters, K. Peters, H. G. von Schnering, E.-U. Würthwein, Liebigs Ann. 1996, 87-98.
    • protonated iminoaziridines: H. Quast, S. Aldenkortt, B. Freudenreich, P. Schäfer, E.-M. Peters, K. Peters, H. G. von Schnering, E.-U. Würthwein, Liebigs Ann. 1996, 87-98.
  • 57
    • 68049147137 scopus 로고    scopus 로고
    • [7c]
    • [7c]
  • 71
    • 84982072008 scopus 로고    scopus 로고
    • K. Peters, H. G. von Schnering, Chem. Ber. 1976, 109, 13841388.
    • K. Peters, H. G. von Schnering, Chem. Ber. 1976, 109, 13841388.
  • 73
    • 0012765132 scopus 로고    scopus 로고
    • 3aH-Benzimidazoles have previously been, postulated as elusive intermediates:a C. W Rees, Pure Appl. Chem. 1979, 51, 12431253;
    • 3aH-Benzimidazoles have previously been, postulated as elusive intermediates:a) C. W Rees, Pure Appl. Chem. 1979, 51, 12431253;
  • 77
    • 68049142840 scopus 로고    scopus 로고
    • Restricted rotation of tert-butyl groups at low temperatures has often been documented: S. Sternhell, Rotation About Single Bonds in Organic Molecules, in Dynamic Nuclear Magnetic Resonance Spectroscopy (Eds.: L. M. Jackman, F. A. Cotton), 1st ed., Academic Press, New York, 1975, chapter 6, pp. 163201.
    • Restricted rotation of tert-butyl groups at low temperatures has often been documented: S. Sternhell, "Rotation About Single Bonds in Organic Molecules", in Dynamic Nuclear Magnetic Resonance Spectroscopy (Eds.: L. M. Jackman, F. A. Cotton), 1st ed., Academic Press, New York, 1975, chapter 6, pp. 163201.
  • 78
    • 84984198838 scopus 로고    scopus 로고
    • These results are in accord with scrambling of labeled substituents in the photodenitrogeiiation products of phenyl-substituted 5-inimo-4,5-dihydro-lH- tetrazoles: Ii. Quast, A. Fuß, U. Nahr, Chem. Ber. 1985, 118, 2164-2185
    • These results are in accord with scrambling of labeled substituents in the photodenitrogeiiation products of phenyl-substituted 5-inimo-4,5-dihydro-lH- tetrazoles: Ii. Quast, A. Fuß, U. Nahr, Chem. Ber. 1985, 118, 2164-2185.
  • 79
    • 0001409032 scopus 로고    scopus 로고
    • J. C. Gilbert, J. R. Butler, J. Am. Chem. Soc. 1970, 92, 21682169.
    • J. C. Gilbert, J. R. Butler, J. Am. Chem. Soc. 1970, 92, 21682169.
  • 80
    • 68049134392 scopus 로고    scopus 로고
    • For the similar ring-expansion of 2,2-diphenyl-N-tosyliminothiirane, see ref.[lb
    • [lb]
  • 81
    • 33750830141 scopus 로고    scopus 로고
    • Related azomethine mines are invoked as intermediates of the formation of indazoles by addition of unsaturated carbenes at aromatic azo compounds: a P. J. Stang, M. G. Mangum, J. Am. Chem Soc, 1977, 99, 2597-2601;
    • Related azomethine mines are invoked as intermediates of the formation of indazoles by addition of unsaturated carbenes at aromatic azo compounds: a) P. J. Stang, M. G. Mangum, J. Am. Chem Soc, 1977, 99, 2597-2601;
  • 83
    • 33645410218 scopus 로고    scopus 로고
    • For a recent review on azomethine imines, see:, Ed, A. Padwa, Thieme, Stuttgart
    • For a recent review on azomethine imines, see: J. G. Schantl, Science of Synthesis, vol. 27 (Ed.: A. Padwa), Thieme, Stuttgart, 2004, pp. 731-824.
    • (2004) Science of Synthesis , vol.27 , pp. 731-824
    • Schantl, J.G.1
  • 84
    • 68049126001 scopus 로고    scopus 로고
    • [7d]
    • [7d]
  • 85
    • 37049140638 scopus 로고    scopus 로고
    • A similar mechanism has been proposed, for the oxidation of N, N' -diphenylsulfamide with sodium hypochlorite/sodium carbonate to afford 5H-dibenzo[c,e][l,2,7]thiadiazepin.e 6,6-di.oxide, see: D. L. Forster, T. L. Gilchrist, C. W. Rees, J. Chem. Soc. C 1971, 993-999.
    • A similar mechanism has been proposed, for the oxidation of N, N' -diphenylsulfamide with sodium hypochlorite/sodium carbonate to afford 5H-dibenzo[c,e][l,2,7]thiadiazepin.e 6,6-di.oxide, see: D. L. Forster, T. L. Gilchrist, C. W. Rees, J. Chem. Soc. C 1971, 993-999.
  • 88
    • 68049126000 scopus 로고    scopus 로고
    • Divinylcy-clopropane/cycloheptadiene and heteroanalogous rearrangements that involve one vinyl group confined in an aromatic ring are known, 36a, 36b] However, we are unaware of examples in which this applies to both vinyl groups
    • [36a, 36b] However, we are unaware of examples in which this applies to both vinyl groups.
  • 89
    • 84982057542 scopus 로고    scopus 로고
    • For thermal [3.5] sigmatropic shifts, see: a K. Dimroth, O. Schaffer, G. Weiershäuser, Chem. Ber. 1981, 114, 1752-1766;
    • For thermal [3.5] sigmatropic shifts, see: a) K. Dimroth, O. Schaffer, G. Weiershäuser, Chem. Ber. 1981, 114, 1752-1766;
  • 96
    • 0033556194 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999, 38, 189-193;
    • (1999) Angew. Chem. Int. Ed , vol.38 , pp. 189-193
  • 98
    • 0009357440 scopus 로고    scopus 로고
    • Cf. the competing thermal ring-expansions of l-allylidene- 2vinylcyclopropane, which may be considered an archetype of 33: W.E. Billups, W. Y. Chow, K. H. Leavell, E. S. Lewis, J. Org. Chem. 1974, 39, 274-275.
    • Cf. the competing thermal ring-expansions of l-allylidene- 2vinylcyclopropane, which may be considered an archetype of 33: W.E. Billups, W. Y. Chow, K. H. Leavell, E. S. Lewis, J. Org. Chem. 1974, 39, 274-275.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.