Synthesis 2015; 47(06): 801-806
DOI: 10.1055/s-0034-1379638
paper
© Georg Thieme Verlag Stuttgart · New York

A Facile One-Pot Synthesis of Selenoureidopeptides Employing LiAlHSeH through Staudinger Aza-Wittig-Type Reaction

Basavaprabhu,
Kupendra M. Sharanabai
Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Dr. B. R. Ambedkar Veedhi, Bangalore University, Bangalore-560 001, India   Email: hariccb@hotmail.com   Email: sureshbabuvommina@rediffmail.com   Email: ariccb@gmail.com
,
Girish Prabhu
Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Dr. B. R. Ambedkar Veedhi, Bangalore University, Bangalore-560 001, India   Email: hariccb@hotmail.com   Email: sureshbabuvommina@rediffmail.com   Email: ariccb@gmail.com
,
Veladi Panduranga
Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Dr. B. R. Ambedkar Veedhi, Bangalore University, Bangalore-560 001, India   Email: hariccb@hotmail.com   Email: sureshbabuvommina@rediffmail.com   Email: ariccb@gmail.com
,
Vommina V. Sureshbabu*
Peptide Research Laboratory, Department of Studies in Chemistry, Central College Campus, Dr. B. R. Ambedkar Veedhi, Bangalore University, Bangalore-560 001, India   Email: hariccb@hotmail.com   Email: sureshbabuvommina@rediffmail.com   Email: ariccb@gmail.com
› Author Affiliations
Further Information

Publication History

Received: 26 September 2014

Accepted after revision: 17 November 2014

Publication Date:
08 January 2015 (online)


Abstract

A one-pot protocol for the synthesis of selenoureidopeptides employing lithium aluminum hydride hydroselenide (LiAlHSeH) as a selenating agent via a Staudinger aza-Wittig-type reaction is reported. The protocol involves the use of Nα-protected aminoalkyl azides and isothicyanato esters to afford the desired products in good yields. This protocol is a direct approach to the synthesis of selenourea compounds that avoids the synthesis of isoselenocyanates and does not require multistep synthesis.