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Cyanoacetylation of indoles, pyrroles and amines, and synthetic uses of these products
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis is based on an organic synthetic project aimed towards development of small molecules acting on the P2 receptor as well as development of synthetic methods to such molecules (primarily indoles and featuring isatogens in particular). The new methodology includes cyanoacetylation of indoles, pyrroles, amines, and enamines using cyanoacetic acid in acetic anhydride. The molecules obtained (e.g. 3-cyanoacetylindole) could be further functionalized by nitrosation followed by reduction. Cyanoacetylated anilines carrying an appropriate substituent (e.g NO2) could be cyclized to quinoxaline-N-oxides, a class of molecules which have been considered as analogues to isatogens. The molecule 2,2'-pyridylisatogen tosylate (PIT) is particularly interesting within this class because of its documented interaction with the P2 receptor.

Place, publisher, year, edition, pages
Stockholm: Karolinska instiutet , 2005. , 39 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:sh:diva-31953ISBN: 91-7140-269-1 (print)OAI: oai:DiVA.org:sh-31953DiVA: diva2:1071756
Public defence
2005-03-18, 4U, Alfred Nobels allé, Huddinge, 10:00 (English)
Opponent
Supervisors
Available from: 2017-02-06 Created: 2017-02-06 Last updated: 2017-02-06Bibliographically approved
List of papers
1. Oxygenation of 2,3-dihydroindoles
Open this publication in new window or tab >>Oxygenation of 2,3-dihydroindoles
2002 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 58, no 45, 9187-9191 p.Article in journal (Refereed) Published
Abstract [en]

Isatogens (3-oxo-3H-indole 1-oxides) possess interesting biological properties and development of a general method to construct these derivatives has now been developed. Indolines (2,3-dihydroindoles) and isatogens have been prepared in an efficient route starting from indoles substituted in position 2. Reduction of the 2-substituted indoles was performed with tin and hydrochloric acid to give racemic indolines, which were converted to isatogens by 3-chloroperoxybenzoic acid (m-CPBA).

National Category
Chemical Sciences
Identifiers
urn:nbn:se:sh:diva-15774 (URN)10.1016/S0040-4020(02)01198-5 (DOI)000179069000005 ()2-s2.0-0037020798 (Scopus ID)
Available from: 2012-03-08 Created: 2012-03-07 Last updated: 2017-12-07Bibliographically approved
2. Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride
Open this publication in new window or tab >>Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride
2004 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 16, 2760-2765 p.Article in journal (Refereed) Published
Abstract [en]

Cyanoacetic acid was activated with acetic anhydride and when heated this reagent reacted with a variety of both activated and deactivated pyrroles, indoles and aniline derivatives.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:sh:diva-15459 (URN)10.1055/s-2004-831164 (DOI)000225051500029 ()2-s2.0-8744311405 (Scopus ID)
Available from: 2012-02-21 Created: 2012-02-20 Last updated: 2017-12-07Bibliographically approved
3. Reinvestigation of a synthesis of quinoxaline-N-oxides
Open this publication in new window or tab >>Reinvestigation of a synthesis of quinoxaline-N-oxides
(English)Manuscript (preprint) (Other academic)
National Category
Chemical Sciences
Identifiers
urn:nbn:se:sh:diva-31948 (URN)
Note

Som manuskript i avhandling. As manuscript in dissertation.

Available from: 2017-02-06 Created: 2017-02-06 Last updated: 2017-02-06Bibliographically approved
4. Synthetic applications of 3-(cyanoacetyl)indoles and related compounds
Open this publication in new window or tab >>Synthetic applications of 3-(cyanoacetyl)indoles and related compounds
2005 (English)In: Journal of Heterocyclic Chemistry, ISSN 0022-152X, E-ISSN 1943-5193, Vol. 42, no 1, 141-145 p.Article in journal (Refereed) Published
Abstract [en]

Various synthetic applications of 3-(cyanoacetyl)indoles, as well as syntheses of some related indoles, have been investigated. Diethyl 2-(1H-indol-3-yl)-2-oxoethylphosphonate and a methyl derivative thereof have been prepared in one step from indole. Moreover, it was demonstrated that 3-(cyanoacetyl)indoles are useful starting materials for the preparation of for example 3-(1H-indol-3-yl)-3-oxopropanamides, 3-heteroarylindoles or 3-heteroaroylindoles.

National Category
Organic Chemistry
Identifiers
urn:nbn:se:sh:diva-14397 (URN)10.1002/jhet.5570420122 (DOI)000227157500022 ()2-s2.0-17844400315 (Scopus ID)
Note

Som manuskript i avhandling. As manuscript in dissertation.

Available from: 2011-12-21 Created: 2011-12-21 Last updated: 2017-12-08Bibliographically approved
5. Functionalizations of 3-(cyanoacetyl)indole and 2-(cyanoacetyl)pyrrole
Open this publication in new window or tab >>Functionalizations of 3-(cyanoacetyl)indole and 2-(cyanoacetyl)pyrrole
(English)Manuscript (preprint) (Other academic)
National Category
Chemical Sciences
Identifiers
urn:nbn:se:sh:diva-31951 (URN)
Note

Som manuskript i avhandling. As manuscript in dissertation.

Available from: 2017-02-06 Created: 2017-02-06 Last updated: 2017-02-06Bibliographically approved

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