Title:
FLUORINE-CONTAINING HETEROCYCLIC COMPOUND PRODUCTION METHOD, AND FLUORINE-CONTAINING COMPOUND PRODUCTION METHOD
Document Type and Number:
WIPO Patent Application WO/2024/095734
Kind Code:
A1
Abstract:
This fluorine-containing heterocyclic compound production method is for obtaining a compound represented by formula (2) through intramolecular cyclization of a compound represented by formula (1). X1 represents a hydrogen atom, a fluorine atom, or a chlorine atom. R1 represents a hydrogen atom, a halogen atom, or a monovalent organic group having 1-20 carbon atoms. n1 represents an integer of 2-7. Y1's each independently represent a carbon atom optionally having a substituent group, and may be, when 2 or more of said Y1's each have a substituent group, linked to each other to form a ring. Z1 represents a nitrogen atom optionally having a substituent group, an oxygen atom, a sulfur atom, or -S(=O)-. Z2 represents: a group corresponding to Z1; a group identical to Z1; a group in which the substituent group of Z1 is substituted with a hydrogen atom; or a sulfur atom. R2 represents a hydrogen atom, a protecting group, a primary or secondary alkyl group having 1-4 carbon atoms, or R7CO-O-CH2-. R7 represents an alkyl group optionally having a fluorine atom.
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Inventors:
ISHIBASHI YUICHIRO (JP)
ICHIKAWA JUNJI (JP)
FUJITA TAKESHI (JP)
ICHIKAWA JUNJI (JP)
FUJITA TAKESHI (JP)
Application Number:
PCT/JP2023/037110
Publication Date:
May 10, 2024
Filing Date:
October 12, 2023
Export Citation:
Assignee:
AGC INC (JP)
International Classes:
C07D209/10; C07C29/32; C07C33/32; C07C35/52; C07C37/11; C07C39/21; C07C51/363; C07C63/74; C07C209/68; C07C211/52; C07C319/20; C07C323/09; C07D307/79; C07D307/92; C07D311/76; C07D313/08; C07D313/20; C07D333/54
Foreign References:
| CN101265246A | 2008-09-17 |
Other References:
CHUN-LIN LI: "Copper-Catalyzed Thiolation Annulations of 1,4-Dihalides with Sulfides Leading to 2-Trifluoromethyl Benzothiophenes and Benzothiazoles", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 75, no. 20, 15 October 2010 (2010-10-15), pages 7037 - 7040, XP093169022, ISSN: 0022-3263, DOI: 10.1021/jo101675f
MIKHAIL G. MOKRUSHIN: "A new synthesis of substituted 2-trifluoromethylindoles", MENDELEEV COMMUNICATIONS, INSTITUTE OF PHYSICS PUBLISHING, BRISTOL, GB, vol. 18, no. 6, 1 November 2008 (2008-11-01), GB , pages 327 - 328, XP093169025, ISSN: 0959-9436, DOI: 10.1016/j.mencom.2008.11.014
JUNJI ICHIKAWA: "The Nucleophilic 5-endo-trig Cyclization of 1,1-Difluoro-1-alkenes: Ring-Fluorinated Hetero- and Carbocycle Synthesis and Remarkable Effect of the Vinylic Fluorines on the Disfavored Process", SYNTHESIS, GEORG THIEME VERLAG, STUTTGART, DE., vol. 2002, no. 13, 20 September 2002 (2002-09-20), STUTTGART, DE. , pages 1917 - 1936, XP093169033, ISSN: 0039-7881, DOI: 10.1055/s-2002-33912
JUNJI ICHIKAWA: "The nucleophilic 5-endo-trig cyclization of gem-difluoroolefins with homoallylic functional groups: syntheses of ring-fluorinated dihydroheteroaromatics", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, no. 19, 1 January 2000 (2000-01-01), UK , pages 1887 - 1888, XP093169035, ISSN: 1359-7345, DOI: 10.1039/b004978f
WÓJTOWICZ-RAJCHEL HANNA; KORONIAK HENRYK: "Synthesis of 5-fluorovinyl derivatives of pyrimidines via Suzuki–Miyaura coupling and their 1,3-dipolar cycloaddition reactions with nitrones", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, NL, vol. 135, 1 January 1900 (1900-01-01), NL , pages 225 - 230, XP028897550, ISSN: 0022-1139, DOI: 10.1016/j.jfluchem.2011.11.005
PATRICK, T.B. ; AGBOKA, T.Y. ; GORRELL, K.: "Heck reaction with 3-fluoro-3-buten-2-one", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, NL, vol. 129, no. 10, 1 October 2008 (2008-10-01), NL , pages 983 - 985, XP025468244, ISSN: 0022-1139, DOI: 10.1016/j.jfluchem.2008.02.006
YUICHIRO ISHIBASHI: "Two-Step Synthesis of 2-Trifluoromethylated and 2-Difluoromethylated Benzoheteroles Starting from HFO-1224yd( Z ) and HFO-1233yd( Z )", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 24, no. 50, 23 December 2022 (2022-12-23), US , pages 9306 - 9310, XP093169039, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.2c03930
MIKHAIL G. MOKRUSHIN: "A new synthesis of substituted 2-trifluoromethylindoles", MENDELEEV COMMUNICATIONS, INSTITUTE OF PHYSICS PUBLISHING, BRISTOL, GB, vol. 18, no. 6, 1 November 2008 (2008-11-01), GB , pages 327 - 328, XP093169025, ISSN: 0959-9436, DOI: 10.1016/j.mencom.2008.11.014
JUNJI ICHIKAWA: "The Nucleophilic 5-endo-trig Cyclization of 1,1-Difluoro-1-alkenes: Ring-Fluorinated Hetero- and Carbocycle Synthesis and Remarkable Effect of the Vinylic Fluorines on the Disfavored Process", SYNTHESIS, GEORG THIEME VERLAG, STUTTGART, DE., vol. 2002, no. 13, 20 September 2002 (2002-09-20), STUTTGART, DE. , pages 1917 - 1936, XP093169033, ISSN: 0039-7881, DOI: 10.1055/s-2002-33912
JUNJI ICHIKAWA: "The nucleophilic 5-endo-trig cyclization of gem-difluoroolefins with homoallylic functional groups: syntheses of ring-fluorinated dihydroheteroaromatics", CHEMICAL COMMUNICATIONS, ROYAL SOCIETY OF CHEMISTRY, UK, no. 19, 1 January 2000 (2000-01-01), UK , pages 1887 - 1888, XP093169035, ISSN: 1359-7345, DOI: 10.1039/b004978f
WÓJTOWICZ-RAJCHEL HANNA; KORONIAK HENRYK: "Synthesis of 5-fluorovinyl derivatives of pyrimidines via Suzuki–Miyaura coupling and their 1,3-dipolar cycloaddition reactions with nitrones", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, NL, vol. 135, 1 January 1900 (1900-01-01), NL , pages 225 - 230, XP028897550, ISSN: 0022-1139, DOI: 10.1016/j.jfluchem.2011.11.005
PATRICK, T.B. ; AGBOKA, T.Y. ; GORRELL, K.: "Heck reaction with 3-fluoro-3-buten-2-one", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, NL, vol. 129, no. 10, 1 October 2008 (2008-10-01), NL , pages 983 - 985, XP025468244, ISSN: 0022-1139, DOI: 10.1016/j.jfluchem.2008.02.006
YUICHIRO ISHIBASHI: "Two-Step Synthesis of 2-Trifluoromethylated and 2-Difluoromethylated Benzoheteroles Starting from HFO-1224yd( Z ) and HFO-1233yd( Z )", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 24, no. 50, 23 December 2022 (2022-12-23), US , pages 9306 - 9310, XP093169039, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.2c03930
Attorney, Agent or Firm:
TAIYO, NAKAJIMA & KATO (JP)
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