Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines

Dusan Kolarski; Wiktor Szymanski; Ben L. Feringa

doi:10.1021/acs.orglett.7b02361

Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines

Dusan Kolarski, Wiktor Szymanski, Ben L. Feringa

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Abstract

The first general two-step, one-pot syntheticroute to 6-azopurines is presented. Microwave-assistednucleophilic aromatic substitution of protected 6-chloropurineswith hydrazines or hydrazides, followed by metal-free oxidationwith oxygen, gives 6-azopurines in high to excellent yields.Photophysical studies revealed intensive n−π* absorption bandthat makes trans-to-cis photoswitching possible using visiblelight (λ = 530 nm).

Original language	English
Pages (from-to)	5090-5093
Number of pages	4
Journal	Organic letters
Volume	19
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.7b02361
Publication status	Published - 6-Oct-2017

Keywords

REVERSIBLE PHOTOREGULATION
AZOBENZENE PHOTOSWITCHES
PHOTOCHROMIC PROPERTIES
SELICICLIB CYC202
ARYL HYDRAZIDES
R-ROSCOVITINE
CELL-DEATH
DERIVATIVES
INHIBITORS
NUCLEOSIDE

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10.1021/acs.orglett.7b02361Licence: CC BY-NC-ND

Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6‑AzopurinesFinal publisher's version, 745 KBLicence: CC BY-NC-ND

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title = "Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines",

abstract = "The first general two-step, one-pot syntheticroute to 6-azopurines is presented. Microwave-assistednucleophilic aromatic substitution of protected 6-chloropurineswith hydrazines or hydrazides, followed by metal-free oxidationwith oxygen, gives 6-azopurines in high to excellent yields.Photophysical studies revealed intensive n−π* absorption bandthat makes trans-to-cis photoswitching possible using visiblelight (λ = 530 nm).",

keywords = "REVERSIBLE PHOTOREGULATION, AZOBENZENE PHOTOSWITCHES, PHOTOCHROMIC PROPERTIES, SELICICLIB CYC202, ARYL HYDRAZIDES, R-ROSCOVITINE, CELL-DEATH, DERIVATIVES, INHIBITORS, NUCLEOSIDE",

author = "Dusan Kolarski and Wiktor Szymanski and Feringa, {Ben L.}",

year = "2017",

month = oct,

day = "6",

doi = "10.1021/acs.orglett.7b02361",

language = "English",

volume = "19",

pages = "5090--5093",

journal = "Organic letters",

issn = "1523-7060",

publisher = "AMER CHEMICAL SOC INC",

number = "19",

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TY - JOUR

T1 - Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines

AU - Kolarski, Dusan

AU - Szymanski, Wiktor

AU - Feringa, Ben L.

PY - 2017/10/6

Y1 - 2017/10/6

N2 - The first general two-step, one-pot syntheticroute to 6-azopurines is presented. Microwave-assistednucleophilic aromatic substitution of protected 6-chloropurineswith hydrazines or hydrazides, followed by metal-free oxidationwith oxygen, gives 6-azopurines in high to excellent yields.Photophysical studies revealed intensive n−π* absorption bandthat makes trans-to-cis photoswitching possible using visiblelight (λ = 530 nm).

AB - The first general two-step, one-pot syntheticroute to 6-azopurines is presented. Microwave-assistednucleophilic aromatic substitution of protected 6-chloropurineswith hydrazines or hydrazides, followed by metal-free oxidationwith oxygen, gives 6-azopurines in high to excellent yields.Photophysical studies revealed intensive n−π* absorption bandthat makes trans-to-cis photoswitching possible using visiblelight (λ = 530 nm).

KW - REVERSIBLE PHOTOREGULATION

KW - AZOBENZENE PHOTOSWITCHES

KW - PHOTOCHROMIC PROPERTIES

KW - SELICICLIB CYC202

KW - ARYL HYDRAZIDES

KW - R-ROSCOVITINE

KW - CELL-DEATH

KW - DERIVATIVES

KW - INHIBITORS

KW - NUCLEOSIDE

U2 - 10.1021/acs.orglett.7b02361

DO - 10.1021/acs.orglett.7b02361

M3 - Letter

SN - 1523-7060

VL - 19

SP - 5090

EP - 5093

JO - Organic letters

JF - Organic letters

IS - 19

ER -

Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines

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