Synthesis and structural determination of 5H‐benzocyclohepten‐5,8‐imines

John C. Dicesare; Jason P. Burgess; S. Wayne Mascarella; F. Ivy Carroll; Richard B. Rothman

doi:10.1002/jhet.5570310131

Synthesis and structural determination of 5H‐benzocyclohepten‐5,8‐imines

John C. Dicesare
, Jason P. Burgess
, S. Wayne Mascarella
, F. Ivy Carroll
, Richard B. Rothman

Biochemistry, Chemistry & Physics

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

19 Scopus citations

Abstract

<div class="line" id="line-70"> Treatment of 4&hyphen;hydroxy&hyphen; <i> N </i> &hyphen;methylisoquinolinium iodide with triethylamine in tetrahydrofuran or acetonitrile forms 2&hyphen;methyl&hyphen;4&hyphen;oxidoisoquinolinium (2)  <i> in situ. </i>  Once formed, 2 can be trapped with dipolarophiles possessing varying degrees of activation to form the 5 <i> H </i> &hyphen;benzocyclohepten&hyphen;5,8&hyphen;imine ring system. Various 2&hyphen;D nmr experiments were used in the identification of the stereochemical and regiochemical assignments for the ring system.</div><div class="line" id="line-117"> <br/></div><div class="line" id="line-120"> <br/></div>

Original language	American English
Journal	Journal of Heterocyclic Chemistry
Volume	31
DOIs	https://doi.org/10.1002/jhet.5570310131
State	Published - Jan 1994

Disciplines

Physical Sciences and Mathematics
Chemistry

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@article{bc51c38ce4b5496daaa644b2fc85e710,

title = "Synthesis and structural determination of 5H‐benzocyclohepten‐5,8‐imines",

abstract = " Treatment of 4\&hyphen;hydroxy\&hyphen; N \&hyphen;methylisoquinolinium iodide with triethylamine in tetrahydrofuran or acetonitrile forms 2\&hyphen;methyl\&hyphen;4\&hyphen;oxidoisoquinolinium (2)\  in situ. \ Once formed,\ 2\ can be trapped with dipolarophiles possessing varying degrees of activation to form the 5 H \&hyphen;benzocyclohepten\&hyphen;5,8\&hyphen;imine ring system. Various 2\&hyphen;D nmr experiments were used in the identification of the stereochemical and regiochemical assignments for the ring system. ",

author = "Dicesare, \{John C.\} and Burgess, \{Jason P.\} and Mascarella, \{S. Wayne\} and Carroll, \{F. Ivy\} and Rothman, \{Richard B.\}",

note = "Treatment of 4‐hydroxy‐ N‐methylisoquinolinium iodide with triethylamine in tetrahydrofuran or acetonitrile forms 2‐methyl‐4‐oxidoisoquinolinium ( 2) in situ. Once formed, 2 can be trapped with dipolarophiles possessing varying degrees of activation to form the 5 H ‐benzocyclohepten‐5,8‐imine ring system. Various 2‐D nmr experiments were used in the identification of the stereochemical and regiochemical assignments for the ring system.",

year = "1994",

month = jan,

doi = "10.1002/jhet.5570310131",

language = "American English",

volume = "31",

journal = "Journal of Heterocyclic Chemistry",

issn = "0022-152X",

publisher = "John Wiley and Sons Inc.",

}

TY - JOUR

T1 - Synthesis and structural determination of 5H‐benzocyclohepten‐5,8‐imines

AU - Dicesare, John C.

AU - Burgess, Jason P.

AU - Mascarella, S. Wayne

AU - Carroll, F. Ivy

AU - Rothman, Richard B.

N1 - Treatment of 4‐hydroxy‐ N‐methylisoquinolinium iodide with triethylamine in tetrahydrofuran or acetonitrile forms 2‐methyl‐4‐oxidoisoquinolinium ( 2) in situ. Once formed, 2 can be trapped with dipolarophiles possessing varying degrees of activation to form the 5 H ‐benzocyclohepten‐5,8‐imine ring system. Various 2‐D nmr experiments were used in the identification of the stereochemical and regiochemical assignments for the ring system.

PY - 1994/1

Y1 - 1994/1

N2 - Treatment of 4&hyphen;hydroxy&hyphen; N &hyphen;methylisoquinolinium iodide with triethylamine in tetrahydrofuran or acetonitrile forms 2&hyphen;methyl&hyphen;4&hyphen;oxidoisoquinolinium (2)  in situ.  Once formed, 2 can be trapped with dipolarophiles possessing varying degrees of activation to form the 5 H &hyphen;benzocyclohepten&hyphen;5,8&hyphen;imine ring system. Various 2&hyphen;D nmr experiments were used in the identification of the stereochemical and regiochemical assignments for the ring system.

AB - Treatment of 4&hyphen;hydroxy&hyphen; N &hyphen;methylisoquinolinium iodide with triethylamine in tetrahydrofuran or acetonitrile forms 2&hyphen;methyl&hyphen;4&hyphen;oxidoisoquinolinium (2)  in situ.  Once formed, 2 can be trapped with dipolarophiles possessing varying degrees of activation to form the 5 H &hyphen;benzocyclohepten&hyphen;5,8&hyphen;imine ring system. Various 2&hyphen;D nmr experiments were used in the identification of the stereochemical and regiochemical assignments for the ring system.

UR - https://doi.org/10.1002/jhet.5570310131

U2 - 10.1002/jhet.5570310131

DO - 10.1002/jhet.5570310131

M3 - Article

SN - 0022-152X

VL - 31

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

ER -

Synthesis and structural determination of 5H‐benzocyclohepten‐5,8‐imines

Abstract

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