GB701120A - 3-substituted-3, 4-dihydro-coumarins and process for the manufacture thereof - Google Patents

3-substituted-3, 4-dihydro-coumarins and process for the manufacture thereof

Info

Publication number
GB701120A
GB701120A GB688751A GB688751A GB701120A GB 701120 A GB701120 A GB 701120A GB 688751 A GB688751 A GB 688751A GB 688751 A GB688751 A GB 688751A GB 701120 A GB701120 A GB 701120A
Authority
GB
United Kingdom
Prior art keywords
benz
hydroxy
indoline
reacting
acetyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB688751A
Inventor
Aaron Cohen
Basil Heath-Brown
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roche Products Ltd
Original Assignee
Roche Products Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Roche Products Ltd filed Critical Roche Products Ltd
Priority to GB688751A priority Critical patent/GB701120A/en
Publication of GB701120A publication Critical patent/GB701120A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0701120/IV (b)/1> wherein X is a carbalkoxy, carbobenzyloxy, or nitrile radical. They are prepared by reacting a compound of the formula (II) <FORM:0701120/IV (b)/2> with an alkali-metal e.g. sodium derivative of a substituted methane of the general formula CH2(X)Z wherein Z is a carbalkoxy radical. The process may be effected in a solvent e.g. xylene. The compounds of formula II may be obtained by reacting N-aryl-hydroxy azacenaphthene with formaldehyde and a dialkylamine. N-Acyl-hydroxy-azacenaphthene (i.e. N-acyl-4-hydroxy-benz (c : d-indoline)) may be obtained by the process of Specification 700,760. In examples (1) 3-carbethoxy-31, 7-acetyliminomethylene-3, 4-dihydro-5, 6-benz-coumarin is prepared by reacting sodium diethyl malonate and N-acetyl-4-hydroxy-5-dimethylamino - methyl - benz (c:d) - indoline. A yellow impurity is removed by boiling the product with zinc dust and glacial acetic acid; (2) 3-cyano-31, 7-acetyliminomethylene-3, 4-dihydro-5, 6-benz-coumarin is prepared by reacting ethyl cyanoacetate and N-acetyl-4-hydroxy-5-dimethylamino-methyl-benz (c : d) - indoline. N - acetyl - 4 - hydroxy - 5 - dimethylamino - methyl - benz (c:d) - indoline is prepared by reacting N-acetyl-4-hydroxy-benz(c:d)-indoline, dimethylamine and aqueous formaldehyde solution. Specification 276,126, [Class 2 (iii)], is referred to in the Provisional Specification.
GB688751A 1951-03-22 1951-03-22 3-substituted-3, 4-dihydro-coumarins and process for the manufacture thereof Expired GB701120A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB688751A GB701120A (en) 1951-03-22 1951-03-22 3-substituted-3, 4-dihydro-coumarins and process for the manufacture thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB688751A GB701120A (en) 1951-03-22 1951-03-22 3-substituted-3, 4-dihydro-coumarins and process for the manufacture thereof

Publications (1)

Publication Number Publication Date
GB701120A true GB701120A (en) 1953-12-16

Family

ID=9822606

Family Applications (1)

Application Number Title Priority Date Filing Date
GB688751A Expired GB701120A (en) 1951-03-22 1951-03-22 3-substituted-3, 4-dihydro-coumarins and process for the manufacture thereof

Country Status (1)

Country Link
GB (1) GB701120A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111349067A (en) * 2018-12-21 2020-06-30 陕西师范大学 Aggregation-induced emission type fluorescent material and preparation method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111349067A (en) * 2018-12-21 2020-06-30 陕西师范大学 Aggregation-induced emission type fluorescent material and preparation method thereof
CN111349067B (en) * 2018-12-21 2022-05-17 陕西师范大学 Aggregation-induced emission type fluorescent material and preparation method thereof

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