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Title:
OXAZOLOPYRIDINE QUATERNARY AMMONIUM SALT COMPOUND, PREPARATION METHOD THEREFOR AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2018/033019
Kind Code:
A1
Abstract:
The present invention relates to an oxazolopyridine quaternary ammonium salt compound as shown in formula 1, a preparation method therefor and a conversion use thereof as a synthetic intermediate. The provided method for preparing the oxazolopyridine quaternary ammonium salt compound as shown in formula 1 mainly comprises allowing an intramolecular cyclization reaction of a 2-oxyacetal (or ketal)-(substituted) pyridine compound to occur under the action of an acid. The provided conversion use of the oxazolopyridine quaternary ammonium salt compound as shown in formula 1 as a synthetic intermediate mainly comprises reacting same with different nucleophilic reagents to obtain N-substituted pyridone compounds or 2-substituted pyridine compounds.

Inventors:
ZHU WEILIANG (CN)
LI BO (CN)
XUE SUSU (CN)
LI XIAOLONG (CN)
LIU PENG (CN)
ZHANG YONG (CN)
XU ZHIJIAN (CN)
CAI TINGTING (CN)
CHEN KAIXIAN (CN)
Application Number:
PCT/CN2017/096975
Publication Date:
February 22, 2018
Filing Date:
August 11, 2017
Export Citation:
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Assignee:
SHANGHAI INST MATERIA MEDICA CAS (CN)
International Classes:
C07D498/04
Other References:
BO, LI ET AL.: "Regioselectivity and Mechanism of Synthesizing N-Substituted 2-Py-ridones and 2-Substituted Pyridines via Metal-Free C-O and C-N Bond-Cleaving of Oxazoline [3, 2-a] Pyridiniums", SCIENTIFIC REPORTS, vol. 7, no. 41287, 25 January 2017 (2017-01-25), pages 1 - 11, XP055469977, ISSN: 2045-2322
POTAPOV, V.A. ET AL.: "Efficient and Selective Syntheses of Novel Unsaturated Chalcogen Chalcogencontaining Pyridine Derivatives", TETRAHEDRON LETTERS, vol. 57, 19 October 2016 (2016-10-19), pages 5341 - 5343, XP029793223, ISSN: 0040-4039
COX, O. ET AL.: "Synthesis and Complete 1H and 13C Assignments of Thiazolo [3, 2-a] Quinolinium Derivatives", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 36, no. 4, 31 December 1999 (1999-12-31), pages 937 - 942, XP055470002, ISSN: 0022-152X
KIM, D.K. ET AL.: "Synthesis of Thiazolo-and Oxazolo [3, 2-a] Pyridinium Systems (review", CHEMISTRY OF HETEROCYCLIC COMPOUNDS, vol. 27, no. 9, 30 September 1991 (1991-09-30), pages 921 - 929, XP055470004
BARNES, C.L. ET AL.: "Structure of 1-acetoxy-1, 2-dihydrothiazolo [3, 2-a] Quinolinium Perchlorate", ACTA CRYSTALLOGRAPHICA, SECTION C: CRYSTAL STRUCTURE COMMUNICATIONS, vol. C43, no. 9, 31 December 1987 (1987-12-31), pages 1739 - 1742, XP055470017, ISSN: 0108-2701
ULSAKER, G.A. ET AL.: "N-Quaternary Compounds. Part L. Elimination Reactions in Dihydrothiazolo [3, 2-a] Pyridinium Derivates", ACTA CHEMICA SCANDINAVICA , SERIES B: ORGANIC CHEMISTRY AND BIOCHEMISTRY, vol. B32, no. 6, 31 December 1978 (1978-12-31), pages 460 - 462, ISSN: 0302-4369
SYCH, E.D. ET AL.: "Thiazolopyridinium Salts with Active Methyl Groups and Cyanine Dyes Made Thiazolopyridinium Salts with Active Methyl Groups and Cyanine Dyes Made", KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, vol. 10, 31 December 1974 (1974-12-31), pages 1335 - 1337, ISSN: 0132-6244
SYCH, E.D. ET AL.: "Synthesis and Reactions of Some Derivatives of Thiazolino [3, 2-a] Pyridinium Salt", KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, vol. 9, 31 December 1973 (1973-12-31), pages 1254 - 1257, ISSN: 0132-6244
DATABASE CAS 24 July 2008 (2008-07-24), retrieved from STN Database accession no. 1030254-01-3
Attorney, Agent or Firm:
KINGSOUND & PARTNERS (CN)
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