Ultrasound-accelerated Synthesis of N-protected Amino Alkyl Iodides from Amino Alcohols Using P₂I₄ Reagent and its Application in the Synthesis of Amino Alkyl Thiols

Title:Ultrasound-accelerated Synthesis of N-protected Amino Alkyl Iodides from Amino Alcohols Using P₂I₄ Reagent and its Application in the Synthesis of Amino Alkyl Thiols

Volume: 21 Issue: 3

Author(s): Lalithamba H. S.*, Nagendra Govindappa*, Akshitha D. Nagaraja and Aisha Siddekha

Affiliation:

• Department of Chemistry, Siddaganga Institute of Technology, B.H. Road, Tumakuru-572 103, Karnataka, India

• Department of Chemistry, REVA University, Rukmini Knowledge Park, Kattigenahalli, Yelahanka, Bangalore-560064, Karnataka, India

Abstract:

Synthesis of amino acid-derived alkyl iodides results in versatile intermediates for many peptidomimetics, and hence, the approach for their synthesis under neutral conditions was achieved in the present work.

The N-protected amino acids were reduced to amino alcohols under T3P as an activator and NaBH₄ as a reducing partner. Thus, synthesized aminols were sonicated with diphosphorus tetraiodide (P₂I₄) in CS₂ to obtain the N-protected amino alkyliodides.

We established the utilisation of the alkyl iodides by converting them to amino alkyl thiols, which serve as building blocks for many heterocycles and other drug candidates. The ultrasonication medium works effectively for all the intermediates preparation; the conditions are mild, and yields are almost quantitative in all steps.

The synthesized compounds were characterized by ¹H NMR, ¹³C NMR, and HRMS analysis.

Cite this article as:

H. S. Lalithamba*, Govindappa Nagendra*, Nagaraja D. Akshitha and Siddekha Aisha, Ultrasound-accelerated Synthesis of N-protected Amino Alkyl Iodides from Amino Alcohols Using P₂I₄ Reagent and its Application in the Synthesis of Amino Alkyl Thiols, Letters in Organic Chemistry 2024; 21 (3) . https://dx.doi.org/10.2174/1570178620666230913160751