GB1257111A - - Google Patents

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Publication number
GB1257111A
GB1257111A GB1257111DA GB1257111A GB 1257111 A GB1257111 A GB 1257111A GB 1257111D A GB1257111D A GB 1257111DA GB 1257111 A GB1257111 A GB 1257111A
Authority
GB
United Kingdom
Prior art keywords
give
amino
phenylaziridine
aziridine
imino
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
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
Priority claimed from CH1401468A external-priority patent/CH503678A/en
Application filed filed Critical
Publication of GB1257111A publication Critical patent/GB1257111A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/22—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/222—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon triple bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/26—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes

Landscapes

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

Abstract

1,257,111 Acetylenic aldehydes. A.ESCHENMOSER. 11 Sept., 1969 [19 Sept., 1968], No. 44959/69. Addition to 1,211,697. Heading C2C. Acetylenic aldehydes of the formula wherein R 1 and R 3 and/or R 2 and R 3 are directly bonded to each other and R 1 and R 2 may also be directly bonded to each other, R 1 , R 2 and R 3 , which may be the same or different, when bonded to one or two of the other groups R 1 , R 2 , R 3 each representing a bi- or tri-valent organic radical respectively or R 1 and R 2 when not bonded to any of the other groups R 1 , R 2 and R 3 each representing a hydrogen atom or a monovalent organic radical are prepared by fragmenting an imino-aziridine of the formula (wherein R 4 , R 5 , R 6 and R 7 which may be the same or different each represents H, alkyl, alkenyl, cycloalkyl, aryl, alkoxycarbonyl, CN or NO 2 but not all can be H together, or any two or more of R 4 , R 5 , R 6 and R 7 together with the carbon atom(s) to which they are bonded form a ring), with simultaneous evolution of molecular nitrogen. Fragmentation can be achieved thermally or photo-chemically, possibly under the very conditions under which the starting imino-aziridines are formed, e.g. when the corresponding carbonyl compounds are reacted with amino-aziridines. Preferred starting materials are (a) ring compounds with the epoxide group on adjacent ring carbon atoms and the carbonyl group in a side chain in α-position to the epoxide group, which give products which are open chain acetylenic aldehydes or cyclic compounds in which the CHO group and the triple bond are separately located in 2 side chains; and (b) cyclic compounds in which the epoxide group and the carbonyl group are both located in the ring, which give products as in (a). In Examples (1) phenylethylene glycol dimesylate (from the diol and mesyl chloride) is condensed with hydrazine to give 1 -amino-2-phenylaziridine (acetate also described), this with 1,2-epoxy- 1 -propionylcyclohex-4-ene gives a crude hydrazide (iminoaziridine) and this on heating at reduced pressure gives non - 2 - en - 6 - yn - 1 - al and non- 3 - en- 6-yn-1-al which are separated by gas chromatography; (2) hydroxyurethane and 2-nitrobenzenesulphonyl chloride are condensed to give a product C 2 H 5 OOCNHOSO 2 R (where R is 2-nitrophenyl), this is reacted with 7-azabicyclo- [4.1.0]heptane to give the N-ethoxycarbonylamino derivative, this is hydrolysed to 7-amino-7- azabicyclo[4.1.0]heptane, this is reacted with 1 -formyl - 1,2 - epoxycyclopentane (prepared by peroxidation of 1-formyl-cyclopent-1-ene) to give a crude hydrazone (imino-aziridine) and this on gas chromatography fragments to provide hex-5-yn-l-al; (3) 2-methyl-2,3-epoxycyclohexan-l-one and l-amino-2-phenylaziridine are condensed to give a crude hydrazone (iminoaziridine) and this on heating at 150‹ C. and 60 mm. Hg gives styrene and hept-5-yn-l-al; (4) 1 - acetyl - 1,2 - epoxy - cyclopentane (from 1 - acetyl - cyclopent - 1 - ene) and 1 - amino-2- phenylaziridine give via a crude hydrazone (amino-aziridine) the same products as (3); and (5) 2,3-epoxycyclohexanone and l-amino-2- phenylaziridine give via a crude hydrazone (imino-aziridine) hex-5-yn-l-al. Other products prepared are 3#-acetoxy-16-oxo-16,17-seco-#<SP>5</SP>- pregnen-17(20) -yne and its dimethyl acetal; 3 - methoxy - 16 - oxo - 16,17 - seco - #<SP>1</SP>'<SP>3,5</SP>'<SP>(10)</SP>-19- norpregnatrien - 17(20) - yne; 3 - oxo - 17#- acetoxy - 2,3 - seco - 5α - androst - 1 - yne; 1- formylmethyl - 3 - ethynyl - 4,4,8 - trimethylbicyclo - [3.3.0] - octane, dec - 4 - yn - 1 - al; undec - 4 - yn - 1 - al; non - 4 - yn - 1 - al, dodec - 4 - yn - 1 - al; pentadec - 4 - yn - 1 - al; and hept-4-yn-l-al.
GB1257111D 1968-09-19 1969-09-11 Expired GB1257111A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1401468A CH503678A (en) 1966-11-01 1968-09-19 Preparation of alpha-oxo alpha beta-seco beta (gamma)-
DE19691951103 DE1951103A1 (en) 1968-09-19 1969-10-10 Process for the production of aldehydes

Publications (1)

Publication Number Publication Date
GB1257111A true GB1257111A (en) 1971-12-15

Family

ID=25713479

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1257111D Expired GB1257111A (en) 1968-09-19 1969-09-11

Country Status (4)

Country Link
DE (1) DE1951103A1 (en)
FR (1) FR2019463A6 (en)
GB (1) GB1257111A (en)
NL (1) NL6914176A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4052422A (en) * 1974-11-08 1977-10-04 E. R. Squibb & Sons, Inc. 4,5-secopregnane derivatives
US4127589A (en) 1974-11-08 1978-11-28 E. R. Squibb & Sons, Inc. 4,5-Seco-steroids
US4235824A (en) * 1976-07-27 1980-11-25 Naarden International N.V. Method for the preparation of fragrances, and method for the preparation of perfume compositions

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4052422A (en) * 1974-11-08 1977-10-04 E. R. Squibb & Sons, Inc. 4,5-secopregnane derivatives
US4127589A (en) 1974-11-08 1978-11-28 E. R. Squibb & Sons, Inc. 4,5-Seco-steroids
US4235824A (en) * 1976-07-27 1980-11-25 Naarden International N.V. Method for the preparation of fragrances, and method for the preparation of perfume compositions

Also Published As

Publication number Publication date
FR2019463A6 (en) 1970-07-03
NL6914176A (en) 1970-03-23
DE1951103A1 (en) 1971-04-29

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee