Synthesis of 1,3-diazaazulene derivatives of colchicinoids and isocolchicinoids via ipso- or tele-substitution-condensation with amidines
Publication type: Journal Article
Publication date: 1998-11-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Condensation of colchicinoids and isocolchicinoids with amidines in dry benzene affords regioselectively 1,3-diazaazulene derivatives: ipso -substitution-condensation products (e.g. 7 ) are best obtained from cycloheptatrienone-ring deactivated substrates (e.g. 4 ), whereas isomeric tele -substitution-condensation products (e.g. 13 ), are best accessible from cycloheptatrienone-ring activated substrates (e.g. 10 ). Hydroxylic solvents inhibit tele -substitution-condensation, arguably by undergoing protonation in preference of the intermediate σ adduct.
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Cavazza M., PIETRA F. Synthesis of 1,3-diazaazulene derivatives of colchicinoids and isocolchicinoids via ipso- or tele-substitution-condensation with amidines // Tetrahedron. 1998. Vol. 54. No. 46. pp. 14059-14064.
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Cavazza M., PIETRA F. Synthesis of 1,3-diazaazulene derivatives of colchicinoids and isocolchicinoids via ipso- or tele-substitution-condensation with amidines // Tetrahedron. 1998. Vol. 54. No. 46. pp. 14059-14064.
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RIS
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TY - JOUR
DO - 10.1016/s0040-4020(98)00856-4
UR - https://doi.org/10.1016/s0040-4020(98)00856-4
TI - Synthesis of 1,3-diazaazulene derivatives of colchicinoids and isocolchicinoids via ipso- or tele-substitution-condensation with amidines
T2 - Tetrahedron
AU - Cavazza, Marino
AU - PIETRA, FRANCESCO
PY - 1998
DA - 1998/11/01
PB - Elsevier
SP - 14059-14064
IS - 46
VL - 54
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{1998_Cavazza,
author = {Marino Cavazza and FRANCESCO PIETRA},
title = {Synthesis of 1,3-diazaazulene derivatives of colchicinoids and isocolchicinoids via ipso- or tele-substitution-condensation with amidines},
journal = {Tetrahedron},
year = {1998},
volume = {54},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/s0040-4020(98)00856-4},
number = {46},
pages = {14059--14064},
doi = {10.1016/s0040-4020(98)00856-4}
}
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MLA
Copy
Cavazza, Marino, and FRANCESCO PIETRA. “Synthesis of 1,3-diazaazulene derivatives of colchicinoids and isocolchicinoids via ipso- or tele-substitution-condensation with amidines.” Tetrahedron, vol. 54, no. 46, Nov. 1998, pp. 14059-14064. https://doi.org/10.1016/s0040-4020(98)00856-4.