A Domino Approach for the Synthesis of alpha-Iodo-beta-dicarbonyl Compounds from alpha-Epoxycarbonyls / Mahato Sachinta,Chatterjee Rana,Santra Sougata,Zyryanov Grigory V.,Hajra Alakananda,Majee Adinath // CHEMISTRYSELECT. - 2017. - V. 2, l. 22. - P. 6254-6259.

ISSN/EISSN:

2365-6549 / нет данных

Type:

Article

Abstract:

A series of alpha-iodo-beta-dicarbonyl compounds have been synthesized from alpha-epoxycarbonyl compounds through a consecutive reaction by ring opening of epoxide followed by the oxidation in presence of NH2OH center dot HCl and NaIO4. To the best of our knowledge, this is the first time report for the use of alpha-epoxycarbonyls as a key starting material for the synthesis of alpha-iodo-beta-dicarbonyl compounds. Various functional groups are well tolerated under the present reaction conditions. The epoxy carbonyl compound containing alkyl part is also effective for this conversion. The reactions were carried out in open atmosphere and are not sensitive to air and moisture. All of the synthesized compounds have been characterized by spectral and analytical data. The potential synthetic applicability of this method was investigated on a gram scale using the model reaction. The advantages of the present method are operational simplicity, short reaction time, general applicability, good tolerance to scale-up synthesis, as well as readily available reagents. A plausible mechanism has been proposed on the basis of an intermediate isolated from the reaction mixture.

Author keywords:

domino reaction; alpha-epoxycarbonyls; alpha-iodo-beta-dicarbonyls; oxidation; ring opening 1,3-DICARBONYL COMPOUNDS; IODINATION; NH2OH-CENTER-DOT-HCL; 2-AMINOBENZOTHIAZOLE; IMIDAZOHETEROCYCLES; COMBINATION; REAGENT; KETONES; NAIO4

DOI:

10.1002/slct.201700867

Web of Science ID:

ISI:000407471900012

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL 31
Publisher	WILEY-V C H VERLAG GMBH
Address	POSTFACH 101161, 69451 WEINHEIM, GERMANY
Language	English
Keywords-Plus	1,3-DICARBONYL COMPOUNDS; IODINATION; NH2OH-CENTER-DOT-HCL; 2-AMINOBENZOTHIAZOLE; IMIDAZOHETEROCYCLES; COMBINATION; REAGENT; KETONES; NAIO4
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	adinath.majee@visva-bharati.ac.in
Funding-Acknowledgement	DST-RSF {[}INT/RUS/RSF/P-08]; Russian Science Foundation {[}16-43-02020]; Act 211 Government of the Russian Federation {[}02.A03.21.0006]
Funding-Text	A. Majee acknowledges the financial support from the DST-RSF Major Research Project (Ref. No. INT/RUS/RSF/P-08). S. Santra and G. V. Zyryanov thank Russian Science Foundation (Ref. \# 16-43-02020), by Act 211 Government of the Russian Federation (Ref. 02.A03.21.0006). We are thankful to DST-FIST and SAP-DRS programme.
Number-of-Cited-References	19
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	2
Journal-ISO	ChemistrySelect
Doc-Delivery-Number	FD3ZW