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Volumn 56, Issue 9, 2000, Pages 1165-1180

Intramolecular inverse electron demand Diels-Alder reactions of tryptamine with tethered heteroaromatic azadienes

Author keywords

Cycloaddition; Indoles; Tetrazines; Triazines

Indexed keywords

ALKADIENE; ETHYLAMINE; TETRAZINE DERIVATIVE; TRIAZINE DERIVATIVE; TRYPTAMINE;

EID: 0034712239     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00003-X     Document Type: Article
Times cited : (85)

References (74)
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    • NAr displacements of methylthiolate from 1,2,4,5-tetrazines: (a)
    • NAr displacements of methylthiolate from 1,2,4,5-tetrazines: (a) Mangia, A.; Bortesi, F.; Amendola, U. J. Heterocycl. Chem. 1977, 14, 587-593. (b) Seitz, G.; Görge, L.; Dietrich, S. Tetrahedron Lett. 1985, 26, 4355-4358. (c) Panek, J. S.; Zhu, B. Tetrahedron Lett. 1996, 37, 8151-8154. (d) Sakya, S. M.; Groskopf, K. K.; Boger, D. L. Tetrahedron Lett. 1997, 38, 3805-3808. (e) Boger, D. L.; Schaum, R. P.; Garbaccio, R. M. J. Org. Chem. 1998, 63, 6329-6337.
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    • NAr displacements using 3,6-dichloropyridazines to tether dienophiles for intramolecular Diels-Alder reactions: (a)
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    • For similar tethering of carbamates to 2a, see Ref. [9e].
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    • Retro Diels-Alder reactions to release methyl cyanoformate have been reported: (a) Taylor, E. C.; Pont, J. L. J. Org. Chem. 1987, 52, 4287-4292. (b) Boger, D. L.; Dang, Q. J. Org. Chem. 1992, 57, 1631-1633. (c) Boger, D. L.; Menezes, R. F.; Dang, Q. J. Org. Chem. 1992, 57, 4333-4336. (d) Boger, D. L.; Kochanny, M. J. J. Org. Chem. 1994, 59, 4950-4955. (e) Dang, Q.; Brown, B. S.; Erion, M. D. J. Org. Chem. 1996, 61, 5204-5205. (f) Dang, Q.; Liu, Y.; Erion, M. D. J. Am. Chem. Soc. 1999, 121, 5833-5834.
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    • Retro Diels-Alder reactions to release methyl cyanoformate have been reported: (a) Taylor, E. C.; Pont, J. L. J. Org. Chem. 1987, 52, 4287-4292. (b) Boger, D. L.; Dang, Q. J. Org. Chem. 1992, 57, 1631-1633. (c) Boger, D. L.; Menezes, R. F.; Dang, Q. J. Org. Chem. 1992, 57, 4333-4336. (d) Boger, D. L.; Kochanny, M. J. J. Org. Chem. 1994, 59, 4950-4955. (e) Dang, Q.; Brown, B. S.; Erion, M. D. J. Org. Chem. 1996, 61, 5204-5205. (f) Dang, Q.; Liu, Y.; Erion, M. D. J. Am. Chem. Soc. 1999, 121, 5833-5834.
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    • 13C spectra were recorded at 20 and 50°C, duplicate resonances were observed for most carbons due to slowly interconverting rotamers about the carbamate.
    • 13C spectra were recorded at 20 and 50°C, duplicate resonances were observed for most carbons due to slowly interconverting rotamers about the carbamate.
  • 72
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    • 2 (96%) as described in the preparation of 1d, followed by BOC-protection (98%) as described in the preparation of 1b.
    • 2 (96%) as described in the preparation of 1d, followed by BOC-protection (98%) as described in the preparation of 1b.
  • 73
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    • Resonances were severely broadened in the spectra recorded at ambient temperature due to inconverting rotamers
    • Resonances were severely broadened in the spectra recorded at ambient temperature due to inconverting rotamers.


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