Novel rearrangement of purines

A. Barak; I. Agranat

doi:10.1007/BF02002620

Novel rearrangement of purines

A. Barak^*, I. Agranat

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

6-Trichloromethyl-9-methylpurine (1) rearranges to 6-dichloromethyl-9-methyl-8-oxopurine (2) in aqueous mild acidic solution. The rearrangement is rationalized in terms of a reaction involving protonation, covalent hydration, prototropic equilibrium and/or a hydride transfer. An alternative mechanism involving a 'positive' halogen compound and hypochlorous acid as an intermediary is also proposed. Compound 1 condenses with 4,5-diaminopyrimidine to give the purine-pyrimidine Schiff base pair 4.

Original language	English
Pages (from-to)	248-251
Number of pages	4
Journal	Experientia
Volume	41
Issue number	2
DOIs	https://doi.org/10.1007/BF02002620
State	Published - Feb 1985

Keywords

'positive' halogen compound
6-dichloromethyl-9-methyl-8-oxopurine
6-trichloromethyl-9-methyl purine
Purine rearrangement
REDOX reaction
synthetic purine-pyramidine pairs

Access to Document

10.1007/BF02002620

Cite this

@article{a711ee20313f4d23be796e73b1489cba,

title = "Novel rearrangement of purines",

abstract = "6-Trichloromethyl-9-methylpurine (1) rearranges to 6-dichloromethyl-9-methyl-8-oxopurine (2) in aqueous mild acidic solution. The rearrangement is rationalized in terms of a reaction involving protonation, covalent hydration, prototropic equilibrium and/or a hydride transfer. An alternative mechanism involving a 'positive' halogen compound and hypochlorous acid as an intermediary is also proposed. Compound 1 condenses with 4,5-diaminopyrimidine to give the purine-pyrimidine Schiff base pair 4.",

keywords = "'positive' halogen compound, 6-dichloromethyl-9-methyl-8-oxopurine, 6-trichloromethyl-9-methyl purine, Purine rearrangement, REDOX reaction, synthetic purine-pyramidine pairs",

author = "A. Barak and I. Agranat",

year = "1985",

month = feb,

doi = "10.1007/BF02002620",

language = "אנגלית",

volume = "41",

pages = "248--251",

journal = "Experientia",

issn = "0014-4754",

publisher = "Springer Science and Business Media Deutschland GmbH",

number = "2",

}

TY - JOUR

T1 - Novel rearrangement of purines

AU - Barak, A.

AU - Agranat, I.

PY - 1985/2

Y1 - 1985/2

N2 - 6-Trichloromethyl-9-methylpurine (1) rearranges to 6-dichloromethyl-9-methyl-8-oxopurine (2) in aqueous mild acidic solution. The rearrangement is rationalized in terms of a reaction involving protonation, covalent hydration, prototropic equilibrium and/or a hydride transfer. An alternative mechanism involving a 'positive' halogen compound and hypochlorous acid as an intermediary is also proposed. Compound 1 condenses with 4,5-diaminopyrimidine to give the purine-pyrimidine Schiff base pair 4.

AB - 6-Trichloromethyl-9-methylpurine (1) rearranges to 6-dichloromethyl-9-methyl-8-oxopurine (2) in aqueous mild acidic solution. The rearrangement is rationalized in terms of a reaction involving protonation, covalent hydration, prototropic equilibrium and/or a hydride transfer. An alternative mechanism involving a 'positive' halogen compound and hypochlorous acid as an intermediary is also proposed. Compound 1 condenses with 4,5-diaminopyrimidine to give the purine-pyrimidine Schiff base pair 4.

KW - 'positive' halogen compound

KW - 6-dichloromethyl-9-methyl-8-oxopurine

KW - 6-trichloromethyl-9-methyl purine

KW - Purine rearrangement

KW - REDOX reaction

KW - synthetic purine-pyramidine pairs

UR - http://www.scopus.com/inward/record.url?scp=0021972494&partnerID=8YFLogxK

U2 - 10.1007/BF02002620

DO - 10.1007/BF02002620

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

C2 - 3972070

AN - SCOPUS:0021972494

SN - 0014-4754

VL - 41

SP - 248

EP - 251

JO - Experientia

JF - Experientia

IS - 2

ER -

Novel rearrangement of purines

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this