Facile synthesis and structure of novel 2,5-disubstituted 1,3,4-selenadiazoles

Guoxiong Hua; Yang Li; Amy Fuller; Alexandra Martha Zoya Slawin; J Derek Woollins

doi:10.1002/ejoc.200900013

Facile synthesis and structure of novel 2,5-disubstituted 1,3,4-selenadiazoles

Guoxiong Hua, Yang Li, Amy Fuller, Alexandra Martha Zoya Slawin, J Derek Woollins

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

Abstract

The reaction of hydrazide with carbonyl chloride in the presence of sodium carbonates leads to the corresponding 1,2-diacylhydrazines [1a–t, R¹C(O)NHNHC(O)R², R¹ = aryl, R² = aryl or alkyl] in moderate to excellent yield (57–90 %). The latter reacts with 2,4-diphenyl-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent, WR) in refluxing toluene to give a series of new 2,5-disubstituted 1,3,4-selenadiazoles (2a–t, 51–99 % yield). All compounds were characterized spectroscopically and six compounds were characterized crystallographically.

Original language	English
Pages (from-to)	1612-1618
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2009
Issue number	10
DOIs	https://doi.org/10.1002/ejoc.200900013
Publication status	Published - Apr 2009

Keywords

Selenium
Organoselenium chemistry
1,3,4-Selenadiazoles
Woollins' reagent
Ray crystal-structures
P-SE anions
Organoselenium compounds
Selenium heterocycles
Lawessons reagent
Acidic media
Mild-steel
Derivatives
1,3,4-thiadiazoles
1,3,4-oxadiazoles

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Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://dx.doi.org/10.1002/ejoc.200900013
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@article{12d861d937ba4538953d6a500badadcf,

title = "Facile synthesis and structure of novel 2,5-disubstituted 1,3,4-selenadiazoles",

abstract = "The reaction of hydrazide with carbonyl chloride in the presence of sodium carbonates leads to the corresponding 1,2-diacylhydrazines [1a–t, R1C(O)NHNHC(O)R2, R1 = aryl, R2 = aryl or alkyl] in moderate to excellent yield (57–90 \%). The latter reacts with 2,4-diphenyl-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent, WR) in refluxing toluene to give a series of new 2,5-disubstituted 1,3,4-selenadiazoles (2a–t, 51–99 \% yield). All compounds were characterized spectroscopically and six compounds were characterized crystallographically. ",

keywords = "Selenium, Organoselenium chemistry, 1,3,4-Selenadiazoles, Woollins' reagent, Ray crystal-structures, P-SE anions, Organoselenium compounds, Selenium heterocycles, Lawessons reagent, Acidic media, Mild-steel, Derivatives, 1,3,4-thiadiazoles, 1,3,4-oxadiazoles",

author = "Guoxiong Hua and Yang Li and Amy Fuller and Slawin, \{Alexandra Martha Zoya\} and Woollins, \{J Derek\}",

note = "This work is funded by EPSRC UK",

year = "2009",

month = apr,

doi = "10.1002/ejoc.200900013",

language = "English",

volume = "2009",

pages = "1612--1618",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH, Weinheim",

number = "10",

}

TY - JOUR

T1 - Facile synthesis and structure of novel 2,5-disubstituted 1,3,4-selenadiazoles

AU - Hua, Guoxiong

AU - Li, Yang

AU - Fuller, Amy

AU - Slawin, Alexandra Martha Zoya

AU - Woollins, J Derek

N1 - This work is funded by EPSRC UK

PY - 2009/4

Y1 - 2009/4

N2 - The reaction of hydrazide with carbonyl chloride in the presence of sodium carbonates leads to the corresponding 1,2-diacylhydrazines [1a–t, R1C(O)NHNHC(O)R2, R1 = aryl, R2 = aryl or alkyl] in moderate to excellent yield (57–90 %). The latter reacts with 2,4-diphenyl-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent, WR) in refluxing toluene to give a series of new 2,5-disubstituted 1,3,4-selenadiazoles (2a–t, 51–99 % yield). All compounds were characterized spectroscopically and six compounds were characterized crystallographically.

AB - The reaction of hydrazide with carbonyl chloride in the presence of sodium carbonates leads to the corresponding 1,2-diacylhydrazines [1a–t, R1C(O)NHNHC(O)R2, R1 = aryl, R2 = aryl or alkyl] in moderate to excellent yield (57–90 %). The latter reacts with 2,4-diphenyl-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent, WR) in refluxing toluene to give a series of new 2,5-disubstituted 1,3,4-selenadiazoles (2a–t, 51–99 % yield). All compounds were characterized spectroscopically and six compounds were characterized crystallographically.

KW - Selenium

KW - Organoselenium chemistry

KW - 1,3,4-Selenadiazoles

KW - Woollins' reagent

KW - Ray crystal-structures

KW - P-SE anions

KW - Organoselenium compounds

KW - Selenium heterocycles

KW - Lawessons reagent

KW - Acidic media

KW - Mild-steel

KW - Derivatives

KW - 1,3,4-thiadiazoles

KW - 1,3,4-oxadiazoles

UR - https://www.scopus.com/pages/publications/64149120445

U2 - 10.1002/ejoc.200900013

DO - 10.1002/ejoc.200900013

M3 - Article

SN - 1434-193X

VL - 2009

SP - 1612

EP - 1618

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 10

ER -

Facile synthesis and structure of novel 2,5-disubstituted 1,3,4-selenadiazoles

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Keywords

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