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.
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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)
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:
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
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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