Microwave mediated hydrogen deuterium exchange: a rapid synthesis of 2H-substituted benzimidazole

Aromatic deuterium compounds were prepared from the unlabeled parent compounds under microwave irradiation. This novel methodology was applied to the deuterium substituted benzimidazole derivative. Deuterium aromatic substituted compounds were prepared by microwave irradiation of the parent unlabele...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 46; no. 31; pp. 5195 - 5197
Main Authors Vaidyanathan, Srirajan, Surber, Bruce W.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.08.2005
Subjects
Online AccessGet full text

Cover

Loading…
Abstract Aromatic deuterium compounds were prepared from the unlabeled parent compounds under microwave irradiation. This novel methodology was applied to the deuterium substituted benzimidazole derivative. Deuterium aromatic substituted compounds were prepared by microwave irradiation of the parent unlabeled compounds in the presence of deuterium oxide and deuterium chloride. The percentage of deuterium incorporation was investigated under various reaction conditions. A rapid synthesis of 2H-substituted benzimidazole under microwave irradiation is described.
AbstractList Aromatic deuterium compounds were prepared from the unlabeled parent compounds under microwave irradiation. This novel methodology was applied to the deuterium substituted benzimidazole derivative. Deuterium aromatic substituted compounds were prepared by microwave irradiation of the parent unlabeled compounds in the presence of deuterium oxide and deuterium chloride. The percentage of deuterium incorporation was investigated under various reaction conditions. A rapid synthesis of 2H-substituted benzimidazole under microwave irradiation is described.
Author Surber, Bruce W.
Vaidyanathan, Srirajan
Author_xml – sequence: 1
  givenname: Srirajan
  surname: Vaidyanathan
  fullname: Vaidyanathan, Srirajan
– sequence: 2
  givenname: Bruce W.
  surname: Surber
  fullname: Surber, Bruce W.
  email: bruce.surber@abbott.com
BookMark eNp9kEFOwzAQRS1UJNrCDVj4AgmeOE5SFkioAopUxAbWlmNPWldNUtlOoT19XZU1oy_N6j_NvAkZdX2HhNwDS4FB8bBJA4YthjRjTKQxAOyKjKEqecJFBSMyZixnSc747IZMvN-wOEXFxkR9WO36H7VH2qKxKqCh64Nx_Qo7anAI6OzQUvzVa9Wt8JEq6tTOGuoPXVijt572Dc0WiR9qH2wYzoAau6NtrVHHfou35LpRW493f3tKvl9fvuaLZPn59j5_XiYaBLBEozC1mpVNJkyhoC6LxnDIFBcsU3kGxgCUoEQukENdaN1UWDGTg2p4XWUln5L8wo3_eO-wkTtnW-UOEpg8a5IbedEkz5pkTNQUa0-XGsbb9had9Npip6MMhzpI09v_ASci23a8
CitedBy_id crossref_primary_10_1002_ange_200700039
crossref_primary_10_1002_ajoc_202200662
crossref_primary_10_1002_ejoc_201500192
crossref_primary_10_1016_j_tetlet_2014_07_071
crossref_primary_10_1002_anie_200700039
crossref_primary_10_1021_ja300655f
crossref_primary_10_1016_j_molcata_2006_04_071
crossref_primary_10_1016_j_bmc_2009_01_049
crossref_primary_10_1016_j_tetlet_2017_03_045
crossref_primary_10_1021_ol801763j
crossref_primary_10_1246_bcsj_81_278
crossref_primary_10_1016_j_tet_2010_12_007
crossref_primary_10_1039_c2ob25157d
crossref_primary_10_1039_C4QO00333K
crossref_primary_10_3389_fnut_2020_619921
Cites_doi 10.1002/anie.200400655
10.1124/dmd.32.6.647
10.1002/jlcr.2580340308
10.1039/b005724j
10.1016/j.tetasy.2004.11.040
10.1002/jlcr.2580150176
10.1016/j.tetlet.2003.12.002
10.1016/j.tetlet.2005.01.025
10.1351/pac200173010193
10.1016/S0040-4020(01)01216-9
10.1021/jm030505a
ContentType Journal Article
Copyright 2005 Elsevier Ltd
Copyright_xml – notice: 2005 Elsevier Ltd
DBID AAYXX
CITATION
DOI 10.1016/j.tetlet.2005.05.110
DatabaseName CrossRef
DatabaseTitle CrossRef
DatabaseTitleList
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1873-3581
EndPage 5197
ExternalDocumentID 10_1016_j_tetlet_2005_05_110
S0040403905011688
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
ADVLN
AFJKZ
AKRWK
CITATION
ID FETCH-LOGICAL-c1510-ce5dba97f25d6a1b76fd312a3502a421dd1171a545e31b6ccf8e80d41af3b8273
IEDL.DBID .~1
ISSN 0040-4039
IngestDate Thu Sep 26 18:30:15 EDT 2024
Fri Feb 23 02:28:32 EST 2024
IsPeerReviewed true
IsScholarly true
Issue 31
Keywords Deuterium
Microwave
Language English
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-c1510-ce5dba97f25d6a1b76fd312a3502a421dd1171a545e31b6ccf8e80d41af3b8273
PageCount 3
ParticipantIDs crossref_primary_10_1016_j_tetlet_2005_05_110
elsevier_sciencedirect_doi_10_1016_j_tetlet_2005_05_110
PublicationCentury 2000
PublicationDate 2005-8-00
PublicationDateYYYYMMDD 2005-08-01
PublicationDate_xml – month: 08
  year: 2005
  text: 2005-8-00
PublicationDecade 2000
PublicationTitle Tetrahedron letters
PublicationYear 2005
Publisher Elsevier Ltd
Publisher_xml – name: Elsevier Ltd
References bib9
Anto, Getvoldsen, Harding, Jones, Lu, Russell, Cioffi, Bell, Le, Koves (bib5) 2000; 16
bib7
Freed, Murphy (bib2) 1978
Varma, Varma (bib4) 2001; 73
bib8
Walsky, Opbach (bib1) 2004; 32
Kim, Varma, Varma, Kappe, Bose, Ganguly, Manhas, Vaidyanathan, Bhattacharjee, Rumthao, Sharma (bib3) 2005; 46
bib6
Cowart, Latshaw, Bhatia, Daanen, Rohde, Nelson, Patel, Kolasa, Nakane, Uchic, Miller, Terranova, Chang, Donnelly-Roberts, Namovic, Hollingsworth, Martino, Lynch, Sullivan, Hsieh, Moreland, Brioni, Stewart (bib10) 2004; 47
Varma (10.1016/j.tetlet.2005.05.110_bib4_1) 2001; 73
Cioffi (10.1016/j.tetlet.2005.05.110_bib5_2) 2005; 16
Walsky (10.1016/j.tetlet.2005.05.110_bib1) 2004; 32
Anto (10.1016/j.tetlet.2005.05.110_bib5_1) 2000
Kim (10.1016/j.tetlet.2005.05.110_bib3_1) 2005; 46
Cowart (10.1016/j.tetlet.2005.05.110_bib10) 2004; 47
Bose (10.1016/j.tetlet.2005.05.110_bib3_4) 2004; 45
Koves (10.1016/j.tetlet.2005.05.110_bib5_3) 1994; 34
Kappe (10.1016/j.tetlet.2005.05.110_bib3_3) 2004; 43
Freed (10.1016/j.tetlet.2005.05.110_bib2) 1978
Varma (10.1016/j.tetlet.2005.05.110_bib3_2) 2002
Varma (10.1016/j.tetlet.2005.05.110_bib4_2) 2002; 58
References_xml – volume: 46
  start-page: 1467
  year: 2005
  ident: bib3
  article-title: Organic Synthesis Using Microwave and Supported Reagents
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Sharma
– volume: 47
  start-page: 3853
  year: 2004
  ident: bib10
  publication-title: J. Med. Chem.
  contributor:
    fullname: Stewart
– ident: bib6
– ident: bib7
– volume: 32
  start-page: 647
  year: 2004
  ident: bib1
  publication-title: Drug Metab. Dispos.
  contributor:
    fullname: Opbach
– ident: bib8
– ident: bib9
– volume: 16
  start-page: 2208
  year: 2000
  ident: bib5
  publication-title: J. Chem. Soc., Perkin Trans. 2
  contributor:
    fullname: Koves
– volume: 73
  start-page: 193
  year: 2001
  ident: bib4
  publication-title: Pure Appl. Chem.
  contributor:
    fullname: Varma
– start-page: 637
  year: 1978
  ident: bib2
  publication-title: J. Labelled Compd. Radiopharm.
  contributor:
    fullname: Murphy
– volume: 43
  start-page: 6250
  year: 2004
  ident: 10.1016/j.tetlet.2005.05.110_bib3_3
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.200400655
  contributor:
    fullname: Kappe
– volume: 32
  start-page: 647
  year: 2004
  ident: 10.1016/j.tetlet.2005.05.110_bib1
  publication-title: Drug Metab. Dispos.
  doi: 10.1124/dmd.32.6.647
  contributor:
    fullname: Walsky
– start-page: 181
  year: 2002
  ident: 10.1016/j.tetlet.2005.05.110_bib3_2
  article-title: Organic Synthesis Using Microwave and Supported Reagents
  contributor:
    fullname: Varma
– volume: 34
  start-page: 255
  year: 1994
  ident: 10.1016/j.tetlet.2005.05.110_bib5_3
  publication-title: J. Labelled Compd. Radiopharm.
  doi: 10.1002/jlcr.2580340308
  contributor:
    fullname: Koves
– start-page: 2208
  year: 2000
  ident: 10.1016/j.tetlet.2005.05.110_bib5_1
  publication-title: J. Chem. Soc., Perkin Trans. 2
  doi: 10.1039/b005724j
  contributor:
    fullname: Anto
– volume: 16
  start-page: 471
  year: 2005
  ident: 10.1016/j.tetlet.2005.05.110_bib5_2
  publication-title: Tetrahedron: Asymmetry
  doi: 10.1016/j.tetasy.2004.11.040
  contributor:
    fullname: Cioffi
– start-page: 637
  year: 1978
  ident: 10.1016/j.tetlet.2005.05.110_bib2
  publication-title: J. Labelled Compd. Radiopharm.
  doi: 10.1002/jlcr.2580150176
  contributor:
    fullname: Freed
– volume: 45
  start-page: 1179
  year: 2004
  ident: 10.1016/j.tetlet.2005.05.110_bib3_4
  publication-title: Tetrahedron Lett.
  doi: 10.1016/j.tetlet.2003.12.002
  contributor:
    fullname: Bose
– volume: 46
  start-page: 1467
  year: 2005
  ident: 10.1016/j.tetlet.2005.05.110_bib3_1
  publication-title: Tetrahedron Lett.
  doi: 10.1016/j.tetlet.2005.01.025
  contributor:
    fullname: Kim
– volume: 73
  start-page: 193
  year: 2001
  ident: 10.1016/j.tetlet.2005.05.110_bib4_1
  publication-title: Pure Appl. Chem.
  doi: 10.1351/pac200173010193
  contributor:
    fullname: Varma
– volume: 58
  start-page: 1235
  year: 2002
  ident: 10.1016/j.tetlet.2005.05.110_bib4_2
  publication-title: Tetrahedron
  doi: 10.1016/S0040-4020(01)01216-9
  contributor:
    fullname: Varma
– volume: 47
  start-page: 3853
  year: 2004
  ident: 10.1016/j.tetlet.2005.05.110_bib10
  publication-title: J. Med. Chem.
  doi: 10.1021/jm030505a
  contributor:
    fullname: Cowart
SSID ssj0000680
Score 1.8106074
Snippet Aromatic deuterium compounds were prepared from the unlabeled parent compounds under microwave irradiation. This novel methodology was applied to the deuterium...
SourceID crossref
elsevier
SourceType Aggregation Database
Publisher
StartPage 5195
SubjectTerms Deuterium
Microwave
Title Microwave mediated hydrogen deuterium exchange: a rapid synthesis of 2H-substituted benzimidazole
URI https://dx.doi.org/10.1016/j.tetlet.2005.05.110
Volume 46
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV07T8MwELYqGGBBPEV5VB5YTe0kTlO2qqIqoHaiUrfoHNsiiKZVH0A78Ns55yEVCTGgZIpiKbo7f_7sfHdHyA2XGjhEkuEe2bIgVJyp0BrmgzWRTTQGgTvvGAzD_ih4HMtxjXSrXBgnqyyxv8D0HK3LJ83Sms1Zmroc3wAv3LNL9zMhcgm_rtgWxvTtl9hC44hXyjn3dpU-l2u8lgYdsixPVqSTxP--PG0tOb1DclByRdopPueI1Ex2TPa6VYu2EwIDJ6f7gHdD8wwQZI_0Za3nU4wKqo3r1pCuJtR8Fum9dxToHGappot1hsRvkS7o1FKvzxYIH4VmQFNlsk06STVspm_mlIx698_dPit7JrAE127OEiO1gnbLelKHIBR6QPvCA19yDwJPaC1ESwDyJuMLFSaJjUzEdSDA-ipCLnNGdrJpZs4JTXgSgTBIGCxOc7AQyBbOV2RMOuGq7dcJq0wVz4rSGHGlGXuNC9O6LpcyxhtNWyetyp7xDxfHiN5_jrz498hLsp_XWs0Ve1dkZzlfmWtkEUvVyMOkQXY7D0_94Tdiqsjw
link.rule.ids 315,783,787,4511,24130,27938,27939,45599,45693
linkProvider Elsevier
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LS8QwEA7retCL-MS3OXgNJm3TzXpbFqW6j9MK3sqkSbCi3WV3ff56J32AgniQ9lQYCJPJN1_SbzKEnHNpgIOSDPfIjkWx5kzHzrIQnFUuMxgE_rxjNI6Tu-j2Xt63SL-phfGyyhr7K0wv0br-clF782KW577GN8IH9-zS_0xQaoWsIhvoYrCv9m4GyfgbICveiOe8QVNBV8q8lhbnZFkfrkiviv89Q33LOtebZKOmi7RXjWiLtGyxTdb6TZe2HQIjr6h7g1dLyyIQJJD04cPMpxgY1FjfsCF_eab2varwvaRA5zDLDV18FMj9FvmCTh0NErZABKlkA4ZqW3zmz7mBz-mT3SV311eTfsLqtgksw_TNWWal0dDtuECaGITGSTChCCCUPIAoEMYI0RGA1MmGQsdZ5pRV3EQCXKgV0pk90i6mhd0nNOOZAmGRMzhc6eAgkh1cskiaTMZ1NzwgrHFVOqtux0gb2dhjWrnWN7qUKb7o2gPSafyZ_pjlFAH8T8vDf1uekbVkMhqmw5vx4Iisl1evlgK-Y9Jezl_sCZKKpT6tg-YLcJHLrQ
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=Microwave+mediated+hydrogen+deuterium+exchange%3A+a+rapid+synthesis+of+2H-substituted+benzimidazole&rft.jtitle=Tetrahedron+letters&rft.au=Vaidyanathan%2C+Srirajan&rft.au=Surber%2C+Bruce+W.&rft.date=2005-08-01&rft.issn=0040-4039&rft.volume=46&rft.issue=31&rft.spage=5195&rft.epage=5197&rft_id=info:doi/10.1016%2Fj.tetlet.2005.05.110&rft.externalDBID=n%2Fa&rft.externalDocID=10_1016_j_tetlet_2005_05_110
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