The synthesis of substituted 1, 8-naphthyridines by the Doebner reaction Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/c247dw93b

Descriptions

Attribute NameValues
Creator
Abstract or Summary
  • The possibility of synthesizing 1, 8-naphthyridines by the Doebner reaction has appeared in many reports. The method involves the introduction of electron releasing groups in the 6-position of 2-amino pyridine to activate the C-3 position. Previously Lewis used 6-methyl-2-amino pyridine with benzaldehyde and pyruvic acid, in an attempt to prepare a 1, 8-naphthyridine. He did not obtain a 1, 8-naphthyridine but an uncyclized product. He attributed his failure to produce a naphthyridine to the weak electron releasing power of the methyl group, which was unable to activate the C-3 position. Nitidandhaprabhas found later that the uncyclized compound lost one molecule of water to give 1(6-methyl-2-pyridyl)-5-phenyl-pyrrolidine-2, 3-dione. Also he found that the use of 2, 6-diaminopyridine in the Doebner reaction did produce a 1, 8-naphthyridine, because of the strong electron releasing power of the amino group. The current work continued the investigation of the effect of electron releasing groups at position 6 in the 2-aminopyridine ring on the formation of 1, 8-naphthyridine. The result showed that 6-hydroxy-2-aminopyridine was also effective in producing ring closure at C-3 to form a 1, 8-naphthyridine. The yield was less than that produced when 2, 6-diamino pyridine was used as the starting material. A second method for the preparation of 1, 8-naphthyridines was developed. Benzalpyruvic acid was prepared and allowed to react with the 6-substituted 2-aminopyridines. By this method the yield of 1, 8-naphthyridines was increased. The effect of different aldehydes in producing 1, 8-naphthyridines by the Doebner reaction was studied. O-methoxy benzaldehyde was used in the reaction in comparision with benzaldehyde. The use of O-methoxy benzaldehyde did produce a better yield. The compounds prepared were substituted 1, 2, 3, 4-tetrahydro-1, 8-naphthyridine-4-carboxylic acid monohydrochlorides. The assigned structures were confirmed on the basis of carbon-hydrogen analysis and the evidence of ultraviolet spectra similar to the spectrum of 6-bromo-2-(methyl amino-methyl)-1, 2, dihydro 1, 8-naphthyridine. This showed two well-defined maxima at 238 and 336 mμ as reported by Zhukova.
Resource Type
Date Available
Date Copyright
Date Issued
Degree Level
Degree Name
Degree Field
Degree Grantor
Commencement Year
Advisor
Academic Affiliation
Non-Academic Affiliation
Keyword
Subject
Rights Statement
Peer Reviewed
Language
Digitization Specifications
  • File scanned at 300 ppi using Capture Perfect 3.0 on a Canon DR-9050C in PDF format. CVista PdfCompressor 5.0 was used for pdf compression and textual OCR.
Replaces
Additional Information
  • description.provenance : Made available in DSpace on 2014-04-14T23:14:00Z (GMT). No. of bitstreams: 1 SamalapaPrasit1967_Redacted.pdf: 647420 bytes, checksum: bee60a4b3dec46fed1cee72758e8b864 (MD5) Previous issue date: 1966-09-07
  • description.provenance : Submitted by Alex McFerrin (amscannerosu@gmail.com) on 2014-04-10T00:03:36Z No. of bitstreams: 1 SamalapaPrasit1967_Redacted.pdf: 647420 bytes, checksum: bee60a4b3dec46fed1cee72758e8b864 (MD5)
  • description.provenance : Approved for entry into archive by Patricia Black(patricia.black@oregonstate.edu) on 2014-04-10T16:22:38Z (GMT) No. of bitstreams: 1 SamalapaPrasit1967_Redacted.pdf: 647420 bytes, checksum: bee60a4b3dec46fed1cee72758e8b864 (MD5)
  • description.provenance : Approved for entry into archive by Katy Davis(kdscannerosu@gmail.com) on 2014-04-14T23:14:00Z (GMT) No. of bitstreams: 1 SamalapaPrasit1967_Redacted.pdf: 647420 bytes, checksum: bee60a4b3dec46fed1cee72758e8b864 (MD5)

Relationships

In Administrative Set:
Last modified: 08/23/2017

Downloadable Content

Download PDF
Citations:

EndNote | Zotero | Mendeley

Items