The synthesis of inward-facing 3,6-di(2-pyridyl)pyridazine ligands

A new class of inward-facing bis(dpp-ligands) fused to rigid molecular racks are reported, eg 17 and 19. The 3,6-di(2-pyridyl)pyridazine ligand units are formed by the reaction of 3,6-di(2-pyridyl) s-tetrazine with molrac bis(olefins), eg 11 and 18 (followed by oxidation of the intermediate dihydrop...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters Vol. 37; no. 16; pp. 2825 - 2828
Main Authors: Butler, Douglas N., Tepperman, Paul M., Gau, Robert A., Warrener, Ronald N.
Format: Journal Article
Language:English
Published: Elsevier Ltd 15-04-1996
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Abstract A new class of inward-facing bis(dpp-ligands) fused to rigid molecular racks are reported, eg 17 and 19. The 3,6-di(2-pyridyl)pyridazine ligand units are formed by the reaction of 3,6-di(2-pyridyl) s-tetrazine with molrac bis(olefins), eg 11 and 18 (followed by oxidation of the intermediate dihydropyridazines); additionally mono-olefin, mono-pyridazines 14 and 21 are reported. Molecular modelling and comments of the mechanism of product formation are included. Rigid mono-and bis-DPP ligands are formed from molrac olefins with tetrazine 1 and DDQ. The steps in the conversion of 11 to 14 and of 14 to 17 are followed by 1H NMR.
AbstractList A new class of inward-facing bis(dpp-ligands) fused to rigid molecular racks are reported, eg 17 and 19. The 3,6-di(2-pyridyl)pyridazine ligand units are formed by the reaction of 3,6-di(2-pyridyl) s-tetrazine with molrac bis(olefins), eg 11 and 18 (followed by oxidation of the intermediate dihydropyridazines); additionally mono-olefin, mono-pyridazines 14 and 21 are reported. Molecular modelling and comments of the mechanism of product formation are included. Rigid mono-and bis-DPP ligands are formed from molrac olefins with tetrazine 1 and DDQ. The steps in the conversion of 11 to 14 and of 14 to 17 are followed by 1H NMR.
Author Tepperman, Paul M.
Butler, Douglas N.
Warrener, Ronald N.
Gau, Robert A.
Author_xml – sequence: 1
  givenname: Douglas N.
  surname: Butler
  fullname: Butler, Douglas N.
– sequence: 2
  givenname: Paul M.
  surname: Tepperman
  fullname: Tepperman, Paul M.
– sequence: 3
  givenname: Robert A.
  surname: Gau
  fullname: Gau, Robert A.
– sequence: 4
  givenname: Ronald N.
  surname: Warrener
  fullname: Warrener, Ronald N.
  organization: Centre for Molecular Architecture, Central Queensland University, Rockhampton, Qld, 4702, Australia
BookMark eNp9kEtLAzEUhYNUsK3-AxezbMHozWQeNxtBiy8ouKnrkMmjjdRMSYoy_vrOWHHp3XxcuOdwz5mQUWiDJeSSwTUDVt0AFEAL4GImqjn0rCmekDHDmlNeIhuR8d_JGZmk9A79VAhjcr_a2Cx1Yb-xyaesdZkPXyoa6pT2YZ3xq4oaP8vprovedNv5D9W3Dzbb-rUKJp2TU6e2yV78ckreHh9Wi2e6fH16WdwtqeZQ7KnTKq_B5Tk2whhmoWwaBIM5MoFaKcwF52AaUZYlN1bxiteuqUrkCKzQwKekOPrq2KYUrZO76D9U7CQDOfQgh5ByCCnFsPQ9SOxlt0eZ7X_79DbKpL0N2hofrd5L0_r_DQ4Y-mTh
CitedBy_id crossref_primary_10_1179_000269805X52887
crossref_primary_10_1002_ange_19961082114
crossref_primary_10_1002_anie_199624851
Cites_doi 10.1080/00397917508061439
10.1039/c39830001340
10.1016/S0040-4039(00)73484-8
10.1039/c39950001417
10.1021/ja00057a019
10.1016/S0040-4039(00)78363-8
10.1016/0040-4020(95)00569-T
10.1002/bscb.19921010702
10.1016/0040-4039(95)01164-D
10.1016/S0040-4039(00)61753-7
10.1021/ja00087a079
10.1071/CH9950241
ContentType Journal Article
Copyright 1996
Copyright_xml – notice: 1996
DBID AAYXX
CITATION
DOI 10.1016/0040-4039(96)00397-8
DatabaseName CrossRef
DatabaseTitle CrossRef
DatabaseTitleList
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1873-3581
EndPage 2828
ExternalDocumentID 10_1016_0040_4039_96_00397_8
0040403996003978
GroupedDBID ---
--K
--M
-ET
-~X
.GJ
.HR
.~1
0R~
123
186
1B1
1RT
1~.
1~5
29Q
3EH
4.4
457
4G.
53G
5VS
6TJ
7-5
71M
85S
8P~
9JM
9JN
AABNK
AACTN
AAEDT
AAEDW
AAIAV
AAIKJ
AAKOC
AALRI
AAOAW
AAQFI
AAQXK
AARLI
AATCM
AAXUO
AAYOK
ABFNM
ABFRF
ABGSF
ABJNI
ABMAC
ABPPZ
ABUDA
ABXDB
ABYKQ
ABZDS
ACBEA
ACBNA
ACDAQ
ACGFS
ACKIV
ACNCT
ACNNM
ACRLP
ADBBV
ADECG
ADEZE
ADMUD
ADUVX
AEBSH
AEFWE
AEHWI
AEKER
AENEX
AFFNX
AFKWA
AFMIJ
AFTJW
AFXIZ
AFZHZ
AGHFR
AGRDE
AGUBO
AGYEJ
AHHHB
AIEXJ
AIKHN
AITUG
AJBFU
AJOXV
AJSZI
ALCLG
ALMA_UNASSIGNED_HOLDINGS
AMFUW
AMRAJ
ASPBG
AVWKF
AXJTR
AZFZN
BKOJK
BLXMC
CS3
D0S
DOVZS
DU5
EBS
EFJIC
EFLBG
EJD
EO8
EO9
EP2
EP3
F5P
FDB
FEDTE
FGOYB
FIRID
FLBIZ
FNPLU
FYGXN
G-Q
G8K
GBLVA
HMS
HVGLF
HZ~
IH2
IHE
J1W
K-O
KOM
M2Z
M41
MO0
MVM
N9A
O-L
O9-
OAUVE
OGGZJ
OHT
OZT
P-8
P-9
P2P
PC.
Q38
R2-
RIG
RNS
ROL
RPZ
SCB
SCC
SDF
SDG
SDP
SES
SEW
SOC
SPC
SPCBC
SSK
SSP
SSU
SSZ
T5K
TN5
TWZ
UQL
WH7
WUQ
XFK
XJT
XPP
XSW
Y6R
YK3
YQJ
YR2
ZCG
ZKB
ZMT
ZXP
~02
~G-
~KM
AAHBH
AAXKI
AAYXX
ABDPE
ADVLN
AFJKZ
AKRWK
CITATION
ID FETCH-LOGICAL-c304t-fca270f228b9dd1e05bb80d828198caa829330db95553dea3637fb65838014c03
ISSN 0040-4039
IngestDate Fri Nov 22 00:58:41 EST 2024
Fri Feb 23 02:27:57 EST 2024
IsPeerReviewed true
IsScholarly true
Issue 16
Language English
LinkModel OpenURL
MergedId FETCHMERGED-LOGICAL-c304t-fca270f228b9dd1e05bb80d828198caa829330db95553dea3637fb65838014c03
PageCount 4
ParticipantIDs crossref_primary_10_1016_0040_4039_96_00397_8
elsevier_sciencedirect_doi_10_1016_0040_4039_96_00397_8
PublicationCentury 1900
PublicationDate 1996-04-15
PublicationDateYYYYMMDD 1996-04-15
PublicationDate_xml – month: 04
  year: 1996
  text: 1996-04-15
  day: 15
PublicationDecade 1990
PublicationTitle Tetrahedron letters
PublicationYear 1996
Publisher Elsevier Ltd
Publisher_xml – name: Elsevier Ltd
References Sauer (BIB5) 1992; 101
Butler, Barrette, Snow (BIB7) 1975
Warrener, R. N.; Liu, L.
Warrener, Abbenante, Kennard, Warrener, Abbenante, Solomon, Russell, Warrener, Elsey, Houghton, Warrener, Elsey, Pitt, Russell, Warrener, Pitt, Butler (BIB2) 1994; 116
Cioslowski, Sauer, Hetzenegger, Karcher, Hierstetter (BIB4) 1993; 115
Butler, Tepperman, Gau, Warrener, Watson, Kashyap (BIB9) 1995; 36
,
Warrener, Elsey, Sankar, Butler, Pekos, Kennard (BIB3) 1994; 35
.
Atkinson, Oliver, Paddon-Row (BIB8) 1993; 34
Voyer, Lamothe (BIB1) 1995; 51
Voyer (10.1016/0040-4039(96)00397-8_BIB1) 1995; 51
Warrener (10.1016/0040-4039(96)00397-8_BIB2_4) 1995; 48
Butler (10.1016/0040-4039(96)00397-8_BIB7) 1975
Sauer (10.1016/0040-4039(96)00397-8_BIB5) 1992; 101
Warrener (10.1016/0040-4039(96)00397-8_BIB3) 1994; 35
Warrener (10.1016/0040-4039(96)00397-8_BIB2_1) 1994; 116
Warrener (10.1016/0040-4039(96)00397-8_BIB2_5) 1983
Warrener (10.1016/0040-4039(96)00397-8_BIB2_2) 1994; 35
Butler (10.1016/0040-4039(96)00397-8_BIB9) 1995; 36
Atkinson (10.1016/0040-4039(96)00397-8_BIB8_1) 1993; 34
Cioslowski (10.1016/0040-4039(96)00397-8_BIB4) 1993; 115
Warrener (10.1016/0040-4039(96)00397-8_BIB2_3) 1995
10.1016/0040-4039(96)00397-8_BIB6
References_xml – volume: 35
  start-page: 6745
  year: 1994
  end-page: 6748
  ident: BIB3
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Kennard
– volume: 51
  start-page: 9241
  year: 1995
  end-page: 9284
  ident: BIB1
  publication-title: Tetrahedron
  contributor:
    fullname: Lamothe
– volume: 34
  start-page: 6147
  year: 1993
  end-page: 6150
  ident: BIB8
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Paddon-Row
– start-page: 101
  year: 1975
  end-page: 106
  ident: BIB7
  publication-title: Syn. Commun.
  contributor:
    fullname: Snow
– volume: 115
  start-page: 1353
  year: 1993
  ident: BIB4
  publication-title: J. Amer. Chem. Soc.
  contributor:
    fullname: Hierstetter
– volume: 101
  start-page: 521
  year: 1992
  end-page: 539
  ident: BIB5
  publication-title: Bull. Soc. Chim. Belg.
  contributor:
    fullname: Sauer
– volume: 116
  start-page: 3645
  year: 1994
  end-page: 3646
  ident: BIB2
  publication-title: J. Amer. Chem. Soc.
  contributor:
    fullname: Butler
– volume: 36
  start-page: 6145
  year: 1995
  end-page: 6148
  ident: BIB9
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Kashyap
– start-page: 101
  year: 1975
  ident: 10.1016/0040-4039(96)00397-8_BIB7
  publication-title: Syn. Commun.
  doi: 10.1080/00397917508061439
  contributor:
    fullname: Butler
– start-page: 1340
  year: 1983
  ident: 10.1016/0040-4039(96)00397-8_BIB2_5
  publication-title: J. Chem. Soc., Chem. Commun.
  doi: 10.1039/c39830001340
  contributor:
    fullname: Warrener
– volume: 35
  start-page: 6745
  year: 1994
  ident: 10.1016/0040-4039(96)00397-8_BIB3
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)73484-8
  contributor:
    fullname: Warrener
– start-page: 1417
  year: 1995
  ident: 10.1016/0040-4039(96)00397-8_BIB2_3
  publication-title: J. Chem. Soc., Chem. Commun.
  doi: 10.1039/c39950001417
  contributor:
    fullname: Warrener
– volume: 115
  start-page: 1353
  year: 1993
  ident: 10.1016/0040-4039(96)00397-8_BIB4
  publication-title: J. Amer. Chem. Soc.
  doi: 10.1021/ja00057a019
  contributor:
    fullname: Cioslowski
– volume: 35
  start-page: 7639
  year: 1994
  ident: 10.1016/0040-4039(96)00397-8_BIB2_2
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)78363-8
  contributor:
    fullname: Warrener
– volume: 51
  start-page: 9241
  year: 1995
  ident: 10.1016/0040-4039(96)00397-8_BIB1
  publication-title: Tetrahedron
  doi: 10.1016/0040-4020(95)00569-T
  contributor:
    fullname: Voyer
– volume: 101
  start-page: 521
  year: 1992
  ident: 10.1016/0040-4039(96)00397-8_BIB5
  publication-title: Bull. Soc. Chim. Belg.
  doi: 10.1002/bscb.19921010702
  contributor:
    fullname: Sauer
– volume: 36
  start-page: 6145
  year: 1995
  ident: 10.1016/0040-4039(96)00397-8_BIB9
  publication-title: Tetrahedron Lett.
  doi: 10.1016/0040-4039(95)01164-D
  contributor:
    fullname: Butler
– ident: 10.1016/0040-4039(96)00397-8_BIB6
– volume: 34
  start-page: 6147
  year: 1993
  ident: 10.1016/0040-4039(96)00397-8_BIB8_1
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)61753-7
  contributor:
    fullname: Atkinson
– volume: 116
  start-page: 3645
  year: 1994
  ident: 10.1016/0040-4039(96)00397-8_BIB2_1
  publication-title: J. Amer. Chem. Soc.
  doi: 10.1021/ja00087a079
  contributor:
    fullname: Warrener
– volume: 48
  start-page: 241
  year: 1995
  ident: 10.1016/0040-4039(96)00397-8_BIB2_4
  publication-title: Aust. J. Chem.
  doi: 10.1071/CH9950241
  contributor:
    fullname: Warrener
SSID ssj0000680
Score 1.5649564
Snippet A new class of inward-facing bis(dpp-ligands) fused to rigid molecular racks are reported, eg 17 and 19. The 3,6-di(2-pyridyl)pyridazine ligand units are...
SourceID crossref
elsevier
SourceType Aggregation Database
Publisher
StartPage 2825
Title The synthesis of inward-facing 3,6-di(2-pyridyl)pyridazine ligands
URI https://dx.doi.org/10.1016/0040-4039(96)00397-8
Volume 37
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwtV3db9MwELe67gFe0PgSg4HyANKm4pHErj8eyygMJPYARewtSmJnqlRlVdc-9L_nLv5IJ00IkHiJ0qtjS3c_ne_Od2dCXtc85dZqS7OqxivMjKVlbhmVAoz9RmQml1iNfP5dXlyqD1M-HQzC1Wo97b9KGmgga6yc_Qtpx0mBAO8gc3iC1OH5x3K_2bZg1_lWI_O2S4xtyhqjAgx4KqiBBcDmXW5Xc7NdvMl199Z1mh4t5leh_DdYrTO7Bp1kzQqgsujqf_rgOiYUrXZM8dHFaYwG2OUSFX8bUhBHX-N_n8pNn9g9mkT6T0wd9kU437q4dZjQ-Fo9gacsrjjTxctCzUyfoNTpYJ6C1-paGJ1ap3aVZBQ7se3qZdcMJuDvlpZVrlja79joNd65G7jARFwQOKuBgLFbLanqd8CYl4hDcSS4dThG7ZH9HBQYH5L9yefp5ZedPV6lIR8TPwhFmZl4F2nHWpz4pe42enYMmdkBeeA9kGTioPOQDGz7iNw7Cxf_PSbvAUJJhFBy3SS3IJSwtwig4wifkx48iQfPE_Lj43R2dk79VRu0Zilf06Yuc5k2ea4qbUxm03FVqdQoPGZVdVmqHANfptLj8ZgZWzLBZFMJPHMHH7tO2VMybK9b-4wkXGeGa9lYsJ05kxYd1szISlkLU0pxSGjgRbF0HVWKkGqIvCuQd4XGH8C7Qh0SGRhWeKvQWXsFiPm3Xz7_5y9fkPs9no_IcL3a2Jdk78ZsXnkk_ALbAXpn
link.rule.ids 315,782,786,27934,27935
linkProvider Elsevier
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=The+synthesis+of+inward-facing+3%2C6-di%282-pyridyl%29pyridazine+ligands&rft.jtitle=Tetrahedron+letters&rft.au=Butler%2C+Douglas+N.&rft.au=Tepperman%2C+Paul+M.&rft.au=Gau%2C+Robert+A.&rft.au=Warrener%2C+Ronald+N.&rft.date=1996-04-15&rft.pub=Elsevier+Ltd&rft.issn=0040-4039&rft.eissn=1873-3581&rft.volume=37&rft.issue=16&rft.spage=2825&rft.epage=2828&rft_id=info:doi/10.1016%2F0040-4039%2896%2900397-8&rft.externalDocID=0040403996003978
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0040-4039&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0040-4039&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0040-4039&client=summon