A facile synthesis of 5(6)-(chloromethyl)benzimidazoles: Replacement of a sulfonic acid functionality by chlorine

Valuable new synthetic intermediates, 5(6)-(chloromethyl)benzimidazoles, were prepared by the facile elimination of sulfur dioxide under the influence of thionyl chloride from benzimidazole-5(6)-methane-sulfonic acids easily obtained from (3,4-diaminophenyl)methanesulfonic acid with formic-, or trif...

Full description

Saved in:
Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 45; no. 2; pp. 343 - 347
Main Authors Pete, Bela, Szokol, Baliant, Toke, Laszlo
Format Journal Article
LanguageEnglish
Published MALDEN Wiley 01.03.2008
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
RECEPTOR
INHIBITORS
BENZIMIDAZOLES
5-CHLOROMETHYL-1H-INDOLE-2-CARBOXYLATES
DERIVATIVES
Online AccessGet more information

Cover

Abstract Valuable new synthetic intermediates, 5(6)-(chloromethyl)benzimidazoles, were prepared by the facile elimination of sulfur dioxide under the influence of thionyl chloride from benzimidazole-5(6)-methane-sulfonic acids easily obtained from (3,4-diaminophenyl)methanesulfonic acid with formic-, or trifluoroacetic acid. Both reaction steps involved only acidic conditions, thus the synthesis of polysubstituted 5(6)-(chloromethyl)benzimidazoles incorporating base-sensitive substituents became possible.
AbstractList Valuable new synthetic intermediates, 5(6)-(chloromethyl)benzimidazoles, were prepared by the facile elimination of sulfur dioxide under the influence of thionyl chloride from benzimidazole-5(6)-methane-sulfonic acids easily obtained from (3,4-diaminophenyl)methanesulfonic acid with formic-, or trifluoroacetic acid. Both reaction steps involved only acidic conditions, thus the synthesis of polysubstituted 5(6)-(chloromethyl)benzimidazoles incorporating base-sensitive substituents became possible.
Author Szokol, Baliant
Toke, Laszlo
Pete, Bela
Author_xml – sequence: 1
  givenname: Bela
  surname: Pete
  fullname: Pete, Bela
  email: bpete@chemres.hu
  organization: Budapest Univ Technol & Econ, Hungarian Acad Sci, Organ Chem Technol Res Grp, H-1521 Budapest, Hungary
– sequence: 2
  givenname: Baliant
  orcidid: 0000-0002-0196-6072
  surname: Szokol
  fullname: Szokol, Baliant
  organization: Budapest Univ Technol & Econ, Hungarian Acad Sci, Organ Chem Technol Res Grp, H-1521 Budapest, Hungary
– sequence: 3
  givenname: Laszlo
  surname: Toke
  fullname: Toke, Laszlo
  organization: Budapest Univ Technol & Econ, Hungarian Acad Sci, Organ Chem Technol Res Grp, H-1521 Budapest, Hungary
BookMark eNqNkMtqwzAQRbVIoUnadbdaJhSnkmxZdnfB9AWBQmmhuyDJI6wgS2mkUJyvr_v4gK5m7sA5XGaGJj54QOiKkhUlhN3sOkgrzgUpOGGkmqDpeGUZ5ez9HM1i3I2R5kJM0ccaG6mtAxwHnzqINuJgMF-Uy2yhOxcOoYfUDW6pwJ9sb1t5Cg7iLX6BvZMaevDpm5A4Hp0J3mo8-lpsjl4nG7x0Ng1YDfhHZj1coDMjXYTLvzlHb_d3r81jtnl-eGrWm0znOa0yRhmRNTOt4HUpKJPUiFpCDbxVXIuKi1JRIxWvOJea0bpgtSQlqKJolWoZm6Pq1_sJKpioLXgN2_3B9vIwbMn4AV4QmpfjRqrGJvndtglHn0b0-v8o-wK7HnH8
CitedBy_id crossref_primary_10_1002_chin_200829124
crossref_primary_10_1016_j_tetlet_2012_09_069
crossref_primary_10_1016_j_tetlet_2016_06_086
Cites_doi 10.1016/j.bmcl.2003.12.051
10.1016/j.bmcl.2003.12.042
10.1016/j.tet.2004.07.038
10.1016/j.bmcl.2005.05.054
10.1016/j.ejmech.2003.11.014
ContentType Journal Article
DBID 1KM
1KN
BLEPL
DTL
GAYFB
DOI 10.1002/jhet.5570450208
DatabaseName Index Chemicus
Current Chemical Reactions
Web of Science Core Collection
Science Citation Index Expanded
Web of Science - Science Citation Index Expanded - 2008
DatabaseTitle Web of Science
DatabaseTitleList Web of Science
Database_xml – sequence: 1
  dbid: 1KN
  name: Current Chemical Reactions
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR
  sourceTypes:
    Enrichment Source
    Index Database
DeliveryMethod no_fulltext_linktorsrc
Discipline Chemistry
EndPage 347
ExternalDocumentID 000254013600008
GroupedDBID ---
-~X
05W
0R~
1KM
1KN
1L6
1OB
1OC
33P
3SF
3WU
4.4
52U
52V
53G
5GY
6TJ
8-0
8-1
8UM
A00
AABCJ
AAESR
AAEVG
AAHHS
AANLZ
AAONW
AASGY
AAXRX
AAZKR
ABCUV
ABJNI
ABQWH
ABXGK
ACAHQ
ACBWZ
ACCFJ
ACCZN
ACFBH
ACGFS
ACGOF
ACIWK
ACMXC
ACNCT
ACPOU
ACXBN
ACXQS
ADBBV
ADBTR
ADEOM
ADIZJ
ADKYN
ADMGS
ADOZA
ADXAS
ADZMN
AEEZP
AEGXH
AEIGN
AEIMD
AENEX
AEQDE
AEUQT
AEUYR
AFBPY
AFFPM
AFGKR
AFPWT
AFZJQ
AHBTC
AI.
AIACR
AITYG
AIURR
AIWBW
AJBDE
ALMA_UNASSIGNED_HOLDINGS
ALUQN
AMBMR
AMYDB
ASPBG
ATUGU
AVWKF
AZFZN
AZVAB
BDRZF
BFHJK
BHBCM
BLEPL
BMXJE
BNHUX
BOGZA
BRXPI
BTSUX
C3M
DCZOG
DRFUL
DRMAN
DRSTM
DTL
EBS
EJD
ESX
F5P
FEDTE
FUBAC
G-S
GODZA
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
HGLYW
HVGLF
HZ~
KBYEO
LATKE
LEEKS
LH4
LITHE
LOXES
LUTES
LW6
LYRES
MEWTI
MRFUL
MRMAN
MRSTM
MSFUL
MSMAN
MSSTM
MXFUL
MXMAN
MXSTM
MY~
NNB
O66
O9-
OIG
P2W
P4E
QRW
ROL
RWI
SJN
SUPJJ
TN5
VH1
WBFHL
WBKPD
WH7
WIH
WIJ
WIK
WOHZO
WXSBR
WYISQ
WYJ
XV2
ZZTAW
~S-
ID FETCH-LOGICAL-c3318-2120a92fd7596712a1f79ae9e5db5c78576b1fab5855ac219429a06eb44dbbd22
ISICitedReferencesCount 3
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000254013600008
ISSN 0022-152X
IngestDate Wed Sep 18 01:22:17 EDT 2024
Fri Nov 08 19:59:25 EST 2024
IsPeerReviewed true
IsScholarly true
Issue 2
Keywords RECEPTOR
INHIBITORS
BENZIMIDAZOLES
5-CHLOROMETHYL-1H-INDOLE-2-CARBOXYLATES
DERIVATIVES
Language English
LinkModel OpenURL
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-c3318-2120a92fd7596712a1f79ae9e5db5c78576b1fab5855ac219429a06eb44dbbd22
ORCID 0000-0002-0196-6072
PageCount 5
ParticipantIDs webofscience_primary_000254013600008CitationCount
webofscience_primary_000254013600008
PublicationCentury 2000
PublicationDate March/April 2008
PublicationDateYYYYMMDD 2008-03-01
PublicationDate_xml – month: 03
  year: 2008
  text: March/April 2008
PublicationDecade 2000
PublicationPlace MALDEN
PublicationPlace_xml – name: MALDEN
PublicationTitle Journal of heterocyclic chemistry
PublicationTitleAbbrev J HETEROCYCLIC CHEM
PublicationYear 2008
Publisher Wiley
Publisher_xml – name: Wiley
References Sun, XW (WOS:000178047100027) 2002; 43
Bates, GB (WOS:A1996UQ52200014) 1996
GRIMMET MR (WOS:000254013600008.8) 1997
Burli, RW (WOS:000189314800039) 2004; 14
He, Y (WOS:000189314800032) 2004; 14
WRIGHT JB (WOS:000254013600008.23) 1951; 48
Deghati, PYF (WOS:000181534900010) 2003; 11
Valdez, J (WOS:000177225500038) 2002; 12
Levesque, S (WOS:000172498400017) 2001; 11
Stefanska, JZ (WOS:000084725900003) 1999; 54
BURTON, DE (WOS:A19657087700031) 1965; 208
Bali, A (WOS:000231186000030) 2005; 15
Pete, B (WOS:000229416400022) 2005; 42
MIDDLETON, RW (WOS:A1980KY53900024) 1980; 17
Rodgers, JD (WOS:A1996VZ84600003) 1996; 6
Wolinowska, Renata (MEDLINE:12588101) 2002; 51
(WOS:000254013600008.1) 1978
Pete, B (WOS:000168404000034) 2001; 42
Pete, B (WOS:000223935100007) 2004; 60
SUN, Q (WOS:A1995RR90400024) 1995; 38
Lopez-Rodriguez, ML (WOS:000086963400019) 2000; 56
MISTRY, AG (WOS:A1986A111500014) 1986; 27
GRIMMETT MR (WOS:000254013600008.7) 1984; 5
Yildiz-Oren, I (WOS:000221067100011) 2004; 39
References_xml – year: 1978
  ident: WOS:000254013600008.1
– volume: 43
  start-page: 7239
  year: 2002
  ident: WOS:000178047100027
  article-title: Synthesis of a novel dimeric bis-benzimidazole with site-selective DNA-binding properties
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: Sun, XW
– volume: 14
  start-page: 1217
  year: 2004
  ident: WOS:000189314800032
  article-title: Synthesis and biological evaluations of novel benzimidazoles as potential antibacterial agents
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2003.12.051
  contributor:
    fullname: He, Y
– volume: 56
  start-page: 3245
  year: 2000
  ident: WOS:000086963400019
  article-title: Pd(0) amination of benzimidazoles as an efficient method towards new (benzimidazolyl)piperazines with high affinity for the 5-HT1A receptor
  publication-title: TETRAHEDRON
  contributor:
    fullname: Lopez-Rodriguez, ML
– year: 1997
  ident: WOS:000254013600008.8
  publication-title: IMIDAZOLE BENZIMIDAZ
  contributor:
    fullname: GRIMMET MR
– volume: 5
  start-page: 457
  year: 1984
  ident: WOS:000254013600008.7
  publication-title: COMPREHENSIVE HETERO
  contributor:
    fullname: GRIMMETT MR
– volume: 12
  start-page: 2221
  year: 2002
  ident: WOS:000177225500038
  article-title: Synthesis and antiparasitic activity of 1H-benzimidazole derivatives
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  contributor:
    fullname: Valdez, J
– volume: 14
  start-page: 1253
  year: 2004
  ident: WOS:000189314800039
  article-title: DNA binding ligands targeting drug-resistant gram-positive bacteria. Part 1: Internal benzimidazole derivatives
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2003.12.042
  contributor:
    fullname: Burli, RW
– volume: 48
  start-page: 396
  year: 1951
  ident: WOS:000254013600008.23
  publication-title: CHEM REV
  contributor:
    fullname: WRIGHT JB
– volume: 60
  start-page: 8829
  year: 2004
  ident: WOS:000223935100007
  article-title: A facile synthesis of 4-, 5- and 6-chloromethyl-1H-indole-2-carboxylates: replacement of a sulfonic acid functionality by chlorine
  publication-title: TETRAHEDRON
  doi: 10.1016/j.tet.2004.07.038
  contributor:
    fullname: Pete, B
– volume: 42
  start-page: 3373
  year: 2001
  ident: WOS:000168404000034
  article-title: Synthesis of 5-substituted indole derivatives. Part 3: A facile synthesis of 5-chloromethyl-1H-indole-2-carboxylates: replacement of sulfonic acid functionality by chlorine
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: Pete, B
– volume: 11
  start-page: 3161
  year: 2001
  ident: WOS:000172498400017
  article-title: Novel bicyclic lactam inhibitors of thrombin: Potency and selectivity optimization through P1 residues
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  contributor:
    fullname: Levesque, S
– volume: 51
  start-page: 265
  year: 2002
  ident: MEDLINE:12588101
  article-title: Antimicrobial activity of substituted 2-trifluoromethyl- and 2-pentafluoroethylbenzimidazoles.
  publication-title: Acta microbiologica Polonica
  contributor:
    fullname: Wolinowska, Renata
– start-page: 1117
  year: 1996
  ident: WOS:A1996UQ52200014
  article-title: Synthesis and solution complexation behaviour of dimeric zinc-selective bis(benzimidazole) derivatives
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
  contributor:
    fullname: Bates, GB
– volume: 54
  start-page: 879
  year: 1999
  ident: WOS:000084725900003
  article-title: Antimicrobial activity of substituted azoles and their nucleosides
  publication-title: PHARMAZIE
  contributor:
    fullname: Stefanska, JZ
– volume: 208
  start-page: 1166
  year: 1965
  ident: WOS:A19657087700031
  article-title: 2-TRIFLUOROMETHYLBENZIMIDAZOLES - A NEW CLASS OF HERBICIDAL COMPOUNDS
  publication-title: NATURE
  contributor:
    fullname: BURTON, DE
– volume: 6
  start-page: 2919
  year: 1996
  ident: WOS:A1996VZ84600003
  article-title: Potent cyclic urea HIV protease inhibitors with benzofused heterocycles as P2/P2' groups
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  contributor:
    fullname: Rodgers, JD
– volume: 38
  start-page: 3638
  year: 1995
  ident: WOS:A1995RR90400024
  article-title: SYNTHESIS AND EVALUATION OF TERBENZIMIDAZOLES AS TOPOISOMERASE-I INHIBITORS
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  contributor:
    fullname: SUN, Q
– volume: 15
  start-page: 3962
  year: 2005
  ident: WOS:000231186000030
  article-title: Design, synthesis, and evaluation of novelly substituted benzimidazole compounds as angiotensin II receptor antagonists
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  doi: 10.1016/j.bmcl.2005.05.054
  contributor:
    fullname: Bali, A
– volume: 39
  start-page: 291
  year: 2004
  ident: WOS:000221067100011
  article-title: Synthesis and structure-activity relationships of new antimicrobial active multi substituted benzazole derivatives
  publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  doi: 10.1016/j.ejmech.2003.11.014
  contributor:
    fullname: Yildiz-Oren, I
– volume: 17
  start-page: 1757
  year: 1980
  ident: WOS:A1980KY53900024
  article-title: SYNTHESIS OF IMIDAZO[4,5-B]PYRIDINES AND [4,5-C]PYRIDINES
  publication-title: JOURNAL OF HETEROCYCLIC CHEMISTRY
  contributor:
    fullname: MIDDLETON, RW
– volume: 11
  start-page: 899
  year: 2003
  ident: WOS:000181534900010
  article-title: Inhibition of nucleoside transport by new analogues of nitrobenzylthioinosine
  publication-title: BIOORGANIC & MEDICINAL CHEMISTRY
  contributor:
    fullname: Deghati, PYF
– volume: 27
  start-page: 1051
  year: 1986
  ident: WOS:A1986A111500014
  article-title: A SUPERIOR SYNTHETIC METHOD FOR THE BROMINATION OF INDOLES AND BENZIMIDAZOLES
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: MISTRY, AG
– volume: 42
  start-page: 615
  year: 2005
  ident: WOS:000229416400022
  article-title: A facile synthesis of 7-chloromethyl-1H-indole-2-carboxylates: Replacement of a sulfonic acid functionality by chlorine
  publication-title: JOURNAL OF HETEROCYCLIC CHEMISTRY
  contributor:
    fullname: Pete, B
SSID ssj0021377
Score 1.8303256
Snippet Valuable new synthetic intermediates, 5(6)-(chloromethyl)benzimidazoles, were prepared by the facile elimination of sulfur dioxide under the influence of...
Source Web of Science
SourceID webofscience
SourceType Enrichment Source
Index Database
StartPage 343
SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title A facile synthesis of 5(6)-(chloromethyl)benzimidazoles: Replacement of a sulfonic acid functionality by chlorine
URI http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000254013600008
Volume 45
WOS 000254013600008
WOSCitedRecordID wos000254013600008
hasFullText
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LT9tAEF4FOJQLorQVUKj2wAFULY3XXjvmlkZFqC29NEi5oX2K0DQGEQ7xL-jPZsbrVwKH0IsTrZLNYz7PfLM7-w0hRw7CkNNRwpJQOBa5VDFlVcQkWkSHPcMtHhS-_BVfXEXfR2LU6fxrVS09ztSpzl88V_I_VoUxsCuekn2FZetJYQCeg33hChaG60o27mO7HLitUXcAiFypLSKANEKqnDJ41DeQj2fYJno-gSFlp_n479jIPKuL4YqqrLokAMvVXdEVB2Y2nzHs-dVCZOtAVYsJq73456T2BqtrMj3XqJ2tq2Zyjf_1zfi-2kkdDX7n2Z-s3PrAJZe6DGdYaoH-lA_5JFtYneg15VmND2z7X0h9gTGM2v7Xy0mWOOMtZxp6AacyLodemfOZy_cSsrfw-05RTiwS2Ha0iW7Vjv5S0KtLEbuFHgAq1xX0eY2sJb2CaP-4rBN3VGWsVOfx21cSUV3-ZelzX6QvBVUZbpOt0hy07wHzlnTsdIe8GVTWeEfu-9QDh9bAoZmj4jg-YcdtyJwsAuaMtuCC75C0ggtFuNAFuFA1pxVc3pOr82_DwQUre28wHYKbZ8BoujLlziQijZOAy8AlqONuhVFCJz1IU1XgpIJsU0gNYQ94jezGcJtHRinD-QeyPs2mdpdQnXBjuY6lhdxbCZnKwAYmilBPn4dC7ZGj9n92fedlVq6XLLNHglVeNiil7VHSYba_2tQfyWaD3QOy4cA_2EMgmzP1qUDCEw9_ges
link.rule.ids 783
linkProvider Clarivate
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=A+facile+synthesis+of+5%286%29-%28chloromethyl%29benzimidazoles%3A+Replacement+of+a+sulfonic+acid+functionality+by+chlorine&rft.jtitle=Journal+of+heterocyclic+chemistry&rft.au=Pete%2C+Bela&rft.au=Szokol%2C+Baliant&rft.au=Toke%2C+Laszlo&rft.date=2008-03-01&rft.pub=Wiley&rft.issn=0022-152X&rft.volume=45&rft.issue=2&rft.spage=343&rft.epage=347&rft_id=info:doi/10.1002%2Fjhet.5570450208&rft.externalDBID=n%2Fa&rft.externalDocID=000254013600008
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0022-152X&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0022-152X&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0022-152X&client=summon