One-pot synthesis of 1-substituted-5-alkylselanyl-1H-tetrazoles from isoselenocyanates: unexpected formation of N-alkyl-N-arylcyanamides and (Z)-Se-alkyl-N-cyano-N,N '-diarylisoselenoureas

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F13%3A39896222" target="_blank" >RIV/00216275:25310/13:39896222 - isvavai.cz</a>

Alternative codes found

RIV/00216208:11160/13:10145894

Result on the web

<a href="http://www.sciencedirect.com/science/article/pii/S0040402013012374" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0040402013012374</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.tet.2013.07.103" target="_blank" >10.1016/j.tet.2013.07.103</a>

Result language

angličtina

Original language name

One-pot synthesis of 1-substituted-5-alkylselanyl-1H-tetrazoles from isoselenocyanates: unexpected formation of N-alkyl-N-arylcyanamides and (Z)-Se-alkyl-N-cyano-N,N '-diarylisoselenoureas

Original language description

1-Substituted-5-alkylsulfanyl-1H-tetrazoles are well known class of organic substances with various applications in medicinal chemistry or photographic industry. Their selenium analogues, 1-substituted-5-alkylselanyl-1H-tetrazoles are, however, much lessexplored because of the lack of suitable methods for their preparation. In this work we investigated the synthesis of 1-alkyl/aryl-5-alkylselanyl-1H-tetrazoles from synthetically available alkyl/arylisoselenocyanates. One-pot reactions of arylisoselenocyanates with sodium azide and alkylating agent led to the target 5-alkylselanyl-1-aryl-1H-tetrazoles but also to interesting side products, namely N-alkyl-N-arylcyanamides and (2)-Se-alkyl-N-cyano-N,N'-diarylisoselenoureas. Nevertheless, when alkylisoselenocyanates were utilized as the substrates, the reactions led exclusively to the formation of 1-alkyl-5-alkylselanyl-1H-tetrazoles in good yields. This simple one-pot procedure brings new possibilities for the preparation of variously s

Czech name

—

Czech description

—

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

—

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2013

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Tetrahedron

ISSN

0040-4020

e-ISSN

—

Volume of the periodical

69

Issue of the periodical within the volume

41

Country of publishing house

GB - UNITED KINGDOM

Number of pages

11

Pages from-to

8798-8808

UT code for WoS article

000324362300016

EID of the result in the Scopus database

—