Method for producing aromatic compound

• US 9,260,451 B2
• Filed: 08/22/2013
• Issued: 02/16/2016
• Est. Priority Date: 08/24/2012
• Status: Active Grant

• Current Assignee: Nippon Kayaku Company Limited
• Original Assignee: Nippon Kayaku Company Limited
• Inventors: Takimiya, Kazuo, Shinamura, Shoji, Hamada, Masahiro, Sadamitsu, Yuichi
• Primary Examiner(s): Leeser, Erich A
• Application Number:
  US14/423,516
• Publication Number:
  US 20150239901A1
• Time in Patent Office: 908 Days
• Field of Search: 549/42
• US Class Current: 1/1
• CPC Class Codes: C07D 493/04 Ortho-condensed systems
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• CPC Class Codes: C07D 495/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C07D 517/04 Ortho-condensed systems
• CPC Class Codes: H10K 85/655 comprising only sulfur as heteroatom
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6574 comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

A method for producing a heterocyclic compound represented by general formula (2) from a heterocyclic compound represented by general formula (1) (in the formulae, X1 represents a halogen atom; each of Y1 and Y2 independently represents an oxygen atom, sulfur atom, or selenium atom; each of R1 and R2 independently represents a substituent; m and n respectively represent the number of substituents R1 and R2, each of m and n representing an integer of 0-4; and when m and n are 2 or higher, R1 and R2 may be the same or different and may bond to each other to form an optionally substituted ring).

Claims

1. A method for manufacturing a heterocyclic compound represented by the general formula (2) from a heterocyclic compound represented by the general formula (1):

2. The method according to claim 1, wherein the compound represented by the general formula (1) is obtained from a compound represented by the general formula (3):

3. The method according to claim 2, wherein the compound represented by the general formula (3) is obtained by reacting a compound represented by the general formula (4) and a compound represented by the general formula (5):

4. The method according to claim 1, wherein Y1 and Y2 each independently represent a sulfur atom or a selenium atom.

5. The method according to claim 1, wherein R1 and R2 are each independently selected from the group consisting of a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxyl group which may have a substituent, a halogen atom, a nitro group, and a cyano group.

6. The method according to claim 1, wherein R1 and R2 are linked to each other so as to form a ring which may have a substituent.

7. The method according to claim 6, wherein the ring formed by linking R1 and R2 to each other which may have a substituent is a benzene ring which may have a substituent or a naphthalene ring which may have a substituent.

8. The method according to claim 2, wherein Y1 and Y2 each independently represent a sulfur atom or a selenium atom.

9. The method according to claim 3, wherein Y1 and Y2 each independently represent a sulfur atom or a selenium atom.

10. The method according to claim 2, wherein R1 and R2 are each independently selected from the group consisting of a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxyl group which may have a substituent, a halogen atom, a nitro group, and a cyano group.

11. The method according to claim 3, wherein R1 and R2 are each independently selected from the group consisting of a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxyl group which may have a substituent, a halogen atom, a nitro group, and a cyano group.

12. The method according to claim 4, wherein R1 and R2 are each independently selected from the group consisting of a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxyl group which may have a substituent, a halogen atom, a nitro group, and a cyano group.

13. The method according to claim 8, wherein R1 and R2 are each independently selected from the group consisting of a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxyl group which may have a substituent, a halogen atom, a nitro group, and a cyano group.

14. The method according to claim 9, wherein R1 and R2 are each independently selected from the group consisting of a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxyl group which may have a substituent, a halogen atom, a nitro group, and a cyano group.

15. The method according to claim 2, wherein R1 and R2 are linked to each other so as to form a ring which may have a substituent.

16. The method according to claim 3, wherein R1 and R2 are linked to each other so as to form a ring which may have a substituent.

17. The method according to claim 4, wherein R1 and R2 are linked to each other so as to form a ring which may have a substituent.

18. The method according to claim 8, wherein R1 and R2 are linked to each other so as to form a ring which may have a substituent.

19. The method according to claim 9, wherein R1 and R2 are linked to each other so as to form a ring which may have a substituent.

20. The method according to claim 15, wherein the ring formed by linking R1 and R2 to each other which may have a substituent is a benzene ring which may have a substituent or a naphthalene ring which may have a substituent.

21. The method according to claim 16, wherein the ring formed by linking R1 and R2 to each other which may have a substituent is a benzene ring which may have a substituent or a naphthalene ring which may have a substituent.

22. The method according to claim 17, wherein the ring formed by linking R1 and R2 to each other which may have a substituent is a benzene ring which may have a substituent or a naphthalene ring which may have a substituent.

23. The method according to claim 18, wherein the ring formed by linking R1 and R2 to each other which may have a substituent is a benzene ring which may have a substituent or a naphthalene ring which may have a substituent.

24. The method according to claim 19, wherein the ring formed by linking R1 and R2 to each other which may have a substituent is a benzene ring which may have a substituent or a naphthalene ring which may have a substituent.