GB790202A - Improvements in and relating to naphthalene derivatives and the manufacture thereof - Google Patents

Improvements in and relating to naphthalene derivatives and the manufacture thereof

Info

Publication number
GB790202A
GB790202A GB1804955A GB1804955A GB790202A GB 790202 A GB790202 A GB 790202A GB 1804955 A GB1804955 A GB 1804955A GB 1804955 A GB1804955 A GB 1804955A GB 790202 A GB790202 A GB 790202A
Authority
GB
United Kingdom
Prior art keywords
naphthalene
diol
formula
oxazine
cyclohexylaminomethyl
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
GB1804955A
Inventor
Walter Mark Duffin
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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 Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB1804955A priority Critical patent/GB790202A/en
Priority to ES0229417A priority patent/ES229417A1/en
Publication of GB790202A publication Critical patent/GB790202A/en
Priority to MY6100069A priority patent/MY6100069A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the formula I: <FORM:0790202/IV (b)/1> acid addition salts thereof (one of R1 and R2 an one of R3 and R4 are hydroxy groups, the remaining groups are each of the formula -CH2NHR5, in which R5 is a straight or branched-chain alkyl group having from 1 to 8 carbon atoms or a cycloalkyl group having from 5 to 7 carbon atoms in the ring), and a process for their preparation by warming a compound of formula II: <FORM:0790202/IV (b)/2> (in which X and Y each represent the grouping -CH2,NR5,CH2,O-) with a mineral acid, or by treating the compound II with mineral acid in the presence of a carbonyl reagent capable of forming an insoluble derivative with formaldehyde, especially 2,4-dinitrophenylhydrazine. The intermediates of formula II are prepared from formalin, naphthalene 1,5-, 1,6- or 2,6-diol and the appropriate amine as described in Specification 790,203. In example: (1) naphthalene-1,6-diol in methanol is added to cyclohexylamine and formalin in methanol at -5 DEG C., the mixture left overnight when the intermediate oxazine separated; a suspension of the oxazine in isopropanol is treated with concentrated HCl and the mixture distilled to remove formaldehyde, leaving 2,5 bis-(cyclohexylaminomethyl)naphthalene - 1,6 - diol dihydrochloride; (2) the intermediate oxazine prepared as in (1) but from naphthalene-1,5-diol is dissolved in chloroform and treated dropwise with alcoholic hydrochloric acid when 2,6-bis(cyclohexylaminomethyl)naphthalene - 1,5 - diol dihydrochloride separates; (3) the intermediate oxazine from naphthalene 2,6-diol is hydrolysed as in (1) to yield 1,5-bis-(cyclohexylaminomethyl) naphthalene - 2,6 - diol hydrochloride; similarly are prepared corresponding compounds derived from: (a) naphthalene-2,6-diol with methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine and n-pentylamine; (b) naphthalene-1,6-diol with ethylamine, n-propylamine, n-butylamine, n-octylamine, cyclopentylamine and cycloheptylamine; and (c) naphthalene-1,5-diol with n-propylamine.
GB1804955A 1955-06-22 1955-06-22 Improvements in and relating to naphthalene derivatives and the manufacture thereof Expired GB790202A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB1804955A GB790202A (en) 1955-06-22 1955-06-22 Improvements in and relating to naphthalene derivatives and the manufacture thereof
ES0229417A ES229417A1 (en) 1955-06-22 1956-06-22 A method of preparation of compounds with antimalaric activity (Machine-translation by Google Translate, not legally binding)
MY6100069A MY6100069A (en) 1955-06-22 1961-12-31 Improvements in and relating to naphthalene derivatives and the manufacture thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1804955A GB790202A (en) 1955-06-22 1955-06-22 Improvements in and relating to naphthalene derivatives and the manufacture thereof

Publications (1)

Publication Number Publication Date
GB790202A true GB790202A (en) 1958-02-05

Family

ID=10105759

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1804955A Expired GB790202A (en) 1955-06-22 1955-06-22 Improvements in and relating to naphthalene derivatives and the manufacture thereof

Country Status (2)

Country Link
GB (1) GB790202A (en)
MY (1) MY6100069A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4822822A (en) * 1985-11-01 1989-04-18 Mitsui Toatsu Chemicals, Inc. Benzylamine derivatives, and use thereof
US4835177A (en) * 1987-06-11 1989-05-30 Merck & Co., Inc. Aminoalkyl naphthalenediols as host resistance enhancers against viral infection
US4894392A (en) * 1987-08-27 1990-01-16 Merck & Co., Inc. Aminoalkyl naphthalenediols as host resistance enhancers
US4923852A (en) * 1987-06-11 1990-05-08 Merck & Co., Inc. Aminoalkyl naphthalenediols as host resistance enhancers against viral infections
EP1457548A1 (en) * 2002-07-30 2004-09-15 Infineum International Limited Oxazines as such and as dispersants in lubricating compositions

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4822822A (en) * 1985-11-01 1989-04-18 Mitsui Toatsu Chemicals, Inc. Benzylamine derivatives, and use thereof
US4835177A (en) * 1987-06-11 1989-05-30 Merck & Co., Inc. Aminoalkyl naphthalenediols as host resistance enhancers against viral infection
US4923852A (en) * 1987-06-11 1990-05-08 Merck & Co., Inc. Aminoalkyl naphthalenediols as host resistance enhancers against viral infections
US4925831A (en) * 1987-06-11 1990-05-15 Merck & Co., Inc. Aminoalkyl naphthalenediols as host resistance enhancers against viral infection
EP0393256A1 (en) * 1987-06-11 1990-10-24 Merck & Co. Inc. Aminoalkyl naphthalenediols as host resistance enhancers against viral infection
US4894392A (en) * 1987-08-27 1990-01-16 Merck & Co., Inc. Aminoalkyl naphthalenediols as host resistance enhancers
EP1457548A1 (en) * 2002-07-30 2004-09-15 Infineum International Limited Oxazines as such and as dispersants in lubricating compositions

Also Published As

Publication number Publication date
MY6100069A (en) 1961-12-31

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