Hexahydro-dibenz[d,f]azecines: Existence of Two Conformational Isomers of the 6-Oxo derivatives in Solution1)

Yoshisuke Tsuda; Masami Murata; Fumiyuki Kiuchi

doi:10.1248/cpb.34.3910

Hexahydro-dibenz[d,f]azecines: Existence of Two Conformational Isomers of the 6-Oxo derivatives in Solution¹⁾

Yoshisuke Tsuda, Masami Murata, Fumiyuki Kiuchi

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

New hexahydro-dibenz[d,f]azecines, 11 and 12, were synthesized from the homoerythrinan-enone 3. Their 6-oxo derivatives were shown to exist in two conformations in solution due to the rotational isomerism of the ten-membered lactam group. An example of remarkably large separation of two methylenedioxy protons in the proton nuclear magnetic resonance spectrum due to their non-equivalence is also presented.

Original language	English
Pages (from-to)	3910-3914
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	34
Issue number	9
DOIs	https://doi.org/10.1248/cpb.34.3910
Publication status	Published - 1986
Externally published	Yes

Keywords

dibenz[d
f]-azecine tetrahydro-dibenz[d
f]azecin-6(5h)-one conformational isomer rotational isomerism ten-membered lactam methylenedioxy group ]H-NMR
f]azecine alkaloid homoerythrinan-enone hexahydro-dibenz[d

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

Access to Document

10.1248/cpb.34.3910

Cite this

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title = "Hexahydro-dibenz[d,f]azecines: Existence of Two Conformational Isomers of the 6-Oxo derivatives in Solution1)",

abstract = "New hexahydro-dibenz[d,f]azecines, 11 and 12, were synthesized from the homoerythrinan-enone 3. Their 6-oxo derivatives were shown to exist in two conformations in solution due to the rotational isomerism of the ten-membered lactam group. An example of remarkably large separation of two methylenedioxy protons in the proton nuclear magnetic resonance spectrum due to their non-equivalence is also presented.",

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author = "Yoshisuke Tsuda and Masami Murata and Fumiyuki Kiuchi",

year = "1986",

doi = "10.1248/cpb.34.3910",

language = "English",

volume = "34",

pages = "3910--3914",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "9",

}

TY - JOUR

T1 - Hexahydro-dibenz[d,f]azecines

T2 - Existence of Two Conformational Isomers of the 6-Oxo derivatives in Solution1)

AU - Tsuda, Yoshisuke

AU - Murata, Masami

AU - Kiuchi, Fumiyuki

PY - 1986

Y1 - 1986

N2 - New hexahydro-dibenz[d,f]azecines, 11 and 12, were synthesized from the homoerythrinan-enone 3. Their 6-oxo derivatives were shown to exist in two conformations in solution due to the rotational isomerism of the ten-membered lactam group. An example of remarkably large separation of two methylenedioxy protons in the proton nuclear magnetic resonance spectrum due to their non-equivalence is also presented.

AB - New hexahydro-dibenz[d,f]azecines, 11 and 12, were synthesized from the homoerythrinan-enone 3. Their 6-oxo derivatives were shown to exist in two conformations in solution due to the rotational isomerism of the ten-membered lactam group. An example of remarkably large separation of two methylenedioxy protons in the proton nuclear magnetic resonance spectrum due to their non-equivalence is also presented.

KW - dibenz[d

KW - f]-azecine tetrahydro-dibenz[d

KW - f]azecin-6(5h)-one conformational isomer rotational isomerism ten-membered lactam methylenedioxy group ]H-NMR

KW - f]azecine alkaloid homoerythrinan-enone hexahydro-dibenz[d

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