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Mono- and Bis-Alkylation of Glyoxal-Bridged Tetraazamacrocycles Using Mechanochemistry.

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Title: Mono- and Bis-Alkylation of Glyoxal-Bridged Tetraazamacrocycles Using Mechanochemistry.
Authors: Abdulwahaab, Bassim H.1, Burke, Benjamin P.1,2, Domarkas, Juozas1,2, Silversides, Jon D.1, Prior, Timothy J.1, Archibald, Stephen J.1,2 S.J.Archibald@Hull.ac.uk
Source: Journal of Organic Chemistry. 2/5/2016, Vol. 81 Issue 3, p890-898. 9p.
Subjects: Alkylation, Glyoxal, Macrocyclic compounds, Mechanical chemistry, Biomolecules, Quaternary ammonium salts
Abstract: Glyoxal-bridged bisaminal tetraazamacrocyclic derivatives of 1,4,7,10-tetraazacyclododecane (cyclen) and 1,4,8,11-tetraazacyclotetradecane (cyclam) can be N-functionalized to incorporate coordinating groups or for conjugation to biomolecules. Herein, we present an improved N-functionalization methodology using mechanochemistry which reduces reaction times in comparison with conventional synthetic routes. A range of six alkyl halides were reacted with cyclen and cyclam bisaminal derivatives in various ratios to form mono- and bis-functionalized quaternary ammonium salts. Cross-bridged cyclam, a key intermediate for CB-TE2A, a commonly used chelator in positron emission tomography medical imaging with 64Cu, has been synthesized using nonconventional synthetic methodologies (grinding and microwave heating) with intermediates characterized by 2D NMR and single crystal XRD. The overall synthesis time of CB-TE2A from cyclam could be shortened to 5 days from the 35 days required for the conventional synthesis. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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Header DbId: egs
DbLabel: Engineering Source
An: 113036707
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
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  Data: Mono- and Bis-Alkylation of Glyoxal-Bridged Tetraazamacrocycles Using Mechanochemistry.
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  Data: <searchLink fieldCode="AR" term="%22Abdulwahaab%2C+Bassim+H%2E%22">Abdulwahaab, Bassim H.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Burke%2C+Benjamin+P%2E%22">Burke, Benjamin P.</searchLink><relatesTo>1,2</relatesTo><br /><searchLink fieldCode="AR" term="%22Domarkas%2C+Juozas%22">Domarkas, Juozas</searchLink><relatesTo>1,2</relatesTo><br /><searchLink fieldCode="AR" term="%22Silversides%2C+Jon+D%2E%22">Silversides, Jon D.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Prior%2C+Timothy+J%2E%22">Prior, Timothy J.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Archibald%2C+Stephen+J%2E%22">Archibald, Stephen J.</searchLink><relatesTo>1,2</relatesTo><i> S.J.Archibald@Hull.ac.uk</i>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 2/5/2016, Vol. 81 Issue 3, p890-898. 9p.
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  Data: <searchLink fieldCode="DE" term="%22Alkylation%22">Alkylation</searchLink><br /><searchLink fieldCode="DE" term="%22Glyoxal%22">Glyoxal</searchLink><br /><searchLink fieldCode="DE" term="%22Macrocyclic+compounds%22">Macrocyclic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Mechanical+chemistry%22">Mechanical chemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Biomolecules%22">Biomolecules</searchLink><br /><searchLink fieldCode="DE" term="%22Quaternary+ammonium+salts%22">Quaternary ammonium salts</searchLink>
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  Data: Glyoxal-bridged bisaminal tetraazamacrocyclic derivatives of 1,4,7,10-tetraazacyclododecane (cyclen) and 1,4,8,11-tetraazacyclotetradecane (cyclam) can be N-functionalized to incorporate coordinating groups or for conjugation to biomolecules. Herein, we present an improved N-functionalization methodology using mechanochemistry which reduces reaction times in comparison with conventional synthetic routes. A range of six alkyl halides were reacted with cyclen and cyclam bisaminal derivatives in various ratios to form mono- and bis-functionalized quaternary ammonium salts. Cross-bridged cyclam, a key intermediate for CB-TE2A, a commonly used chelator in positron emission tomography medical imaging with 64Cu, has been synthesized using nonconventional synthetic methodologies (grinding and microwave heating) with intermediates characterized by 2D NMR and single crystal XRD. The overall synthesis time of CB-TE2A from cyclam could be shortened to 5 days from the 35 days required for the conventional synthesis. [ABSTRACT FROM AUTHOR]
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  Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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RecordInfo BibRecord:
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        Value: 10.1021/acs.joc.5b02464
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      – Code: eng
        Text: English
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        PageCount: 9
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    Subjects:
      – SubjectFull: Alkylation
        Type: general
      – SubjectFull: Glyoxal
        Type: general
      – SubjectFull: Macrocyclic compounds
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      – SubjectFull: Mechanical chemistry
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      – SubjectFull: Biomolecules
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      – SubjectFull: Quaternary ammonium salts
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      – TitleFull: Mono- and Bis-Alkylation of Glyoxal-Bridged Tetraazamacrocycles Using Mechanochemistry.
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              Text: 2/5/2016
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