Complete structural and spectral assignment of oxoisoaporphines by HMQC and HMBC experiments

Eduardo Sobarzo-Sánchez; Bruce K. Cassels; Carolina Jullian; Luis Castedo

doi:10.1002/mrc.1177

Complete structural and spectral assignment of oxoisoaporphines by HMQC and HMBC experiments

Eduardo Sobarzo-Sánchez
, Bruce K. Cassels
, Carolina Jullian
, Luis Castedo

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

9 Scopus citations

Abstract

The oxoisoaporphines 2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one, 2,3-dihydro-5-methoxy-7H-dibenzo [de,h] quinolin-7-one, 5-methoxy-6-hydroxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one, 5,6-dimethoxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one and 5,6-methylenedioxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one were prepared by cyclization of phenylethylaminophthalides with polyphosphoric acid or by treating 1-(2-carboxyphenyl)-3,4-dihydroisoquinoline hydrochloride with sulfuric acid at 0°C. The structures were confirmed and ¹H and ¹³C NMR spectra were completely assigned using a combination of one- and two-dimensional NMR techniques.

Original language	English
Pages (from-to)	296-300
Number of pages	5
Journal	Magnetic Resonance in Chemistry
Volume	41
Issue number	4
DOIs	https://doi.org/10.1002/mrc.1177
State	Published - 1 Apr 2003
Externally published	Yes

Keywords

2,3-dihydro-7H-dibenzo[de,h]quinolin-7-ones
C NMR
H NMR
H-H COSY
HMBC
HMQC
NMR
Oxoisoaporphines

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10.1002/mrc.1177

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title = "Complete structural and spectral assignment of oxoisoaporphines by HMQC and HMBC experiments",

abstract = "The oxoisoaporphines 2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one, 2,3-dihydro-5-methoxy-7H-dibenzo [de,h] quinolin-7-one, 5-methoxy-6-hydroxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one, 5,6-dimethoxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one and 5,6-methylenedioxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one were prepared by cyclization of phenylethylaminophthalides with polyphosphoric acid or by treating 1-(2-carboxyphenyl)-3,4-dihydroisoquinoline hydrochloride with sulfuric acid at 0°C. The structures were confirmed and 1H and 13C NMR spectra were completely assigned using a combination of one- and two-dimensional NMR techniques.",

keywords = "2,3-dihydro-7H-dibenzo[de,h]quinolin-7-ones, C NMR, H NMR, H-H COSY, HMBC, HMQC, NMR, Oxoisoaporphines",

author = "Eduardo Sobarzo-S{\'a}nchez and Cassels, \{Bruce K.\} and Carolina Jullian and Luis Castedo",

year = "2003",

month = apr,

day = "1",

doi = "10.1002/mrc.1177",

language = "English",

volume = "41",

pages = "296--300",

journal = "Magnetic Resonance in Chemistry",

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TY - JOUR

T1 - Complete structural and spectral assignment of oxoisoaporphines by HMQC and HMBC experiments

AU - Sobarzo-Sánchez, Eduardo

AU - Cassels, Bruce K.

AU - Jullian, Carolina

AU - Castedo, Luis

PY - 2003/4/1

Y1 - 2003/4/1

N2 - The oxoisoaporphines 2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one, 2,3-dihydro-5-methoxy-7H-dibenzo [de,h] quinolin-7-one, 5-methoxy-6-hydroxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one, 5,6-dimethoxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one and 5,6-methylenedioxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one were prepared by cyclization of phenylethylaminophthalides with polyphosphoric acid or by treating 1-(2-carboxyphenyl)-3,4-dihydroisoquinoline hydrochloride with sulfuric acid at 0°C. The structures were confirmed and 1H and 13C NMR spectra were completely assigned using a combination of one- and two-dimensional NMR techniques.

AB - The oxoisoaporphines 2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one, 2,3-dihydro-5-methoxy-7H-dibenzo [de,h] quinolin-7-one, 5-methoxy-6-hydroxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one, 5,6-dimethoxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one and 5,6-methylenedioxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one were prepared by cyclization of phenylethylaminophthalides with polyphosphoric acid or by treating 1-(2-carboxyphenyl)-3,4-dihydroisoquinoline hydrochloride with sulfuric acid at 0°C. The structures were confirmed and 1H and 13C NMR spectra were completely assigned using a combination of one- and two-dimensional NMR techniques.

KW - 2,3-dihydro-7H-dibenzo[de,h]quinolin-7-ones

KW - C NMR

KW - H NMR

KW - H-H COSY

KW - HMBC

KW - HMQC

KW - NMR

KW - Oxoisoaporphines

UR - https://www.scopus.com/pages/publications/0037237270

U2 - 10.1002/mrc.1177

DO - 10.1002/mrc.1177

M3 - Article

AN - SCOPUS:0037237270

SN - 0749-1581

VL - 41

SP - 296

EP - 300

JO - Magnetic Resonance in Chemistry

JF - Magnetic Resonance in Chemistry

IS - 4

ER -

Complete structural and spectral assignment of oxoisoaporphines by HMQC and HMBC experiments

Abstract

Keywords

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