Crystal structures of 4-{(E)-3-[(imino-λ5-aza-nyl-idene)amino]-prop-1-en-yl}- N, N-di-methyl-imidazole-1-sulfonamide and 2-[(imino-λ5-aza-nyl-idene)amino]-4-{(E)-3-[(imino-λ5-aza-nyl-idene)amino]-prop-1-en-yl}- N, N-di-methyl-imidazole-1-sulfonamide

Lorenzo M Cruz; Raakiyah Y Moore; Marcela Torres Gutierrez; Apsara K Herath; Carl J Lovely; Muhammed Yousufuddin

doi:10.1107/S205698901900519X

Crystal structures of 4-{(E)-3-[(imino-λ⁵-aza-nyl-idene)amino]-prop-1-en-yl}- N, N-di-methyl-imidazole-1-sulfonamide and 2-[(imino-λ⁵-aza-nyl-idene)amino]-4-{(E)-3-[(imino-λ⁵-aza-nyl-idene)amino]-prop-1-en-yl}- N, N-di-methyl-imidazole-1-sulfonamide

Acta Crystallogr E Crystallogr Commun. 2019 Apr 25;75(Pt 5):695-699. doi: 10.1107/S205698901900519X. eCollection 2019 May 1.

Authors

Lorenzo M Cruz¹, Raakiyah Y Moore¹, Marcela Torres Gutierrez¹, Apsara K Herath², Carl J Lovely², Muhammed Yousufuddin¹

Affiliations

¹ Life and Health Sciences Department, University of North Texas at Dallas, 7400 University Hills Blvd, Dallas, TX 75241, USA.
² Department of Chemistry and Biochemistry, University of Texas at Arlington, 700 Planetarium Pl., Arlington, TX 76019, USA.

Abstract

The structures of two azide containing imidazole derivatives are reported. Allylic azides are fairly reactive making them attractive starting compounds to convert into amides. The first, C₈H₁₂N₆O₂S, contains one azide group with an N_α-N_β distance of 1.229 (2) Å and an N_β-N_γ distance of 1.128 (2) Å. The second, C₈H₁₁N₉O₂S, contains two azide groups with an average N_α-N_β distance of 1.249 (2) Å and an average N_β-N_γ distance of 1.132 (2) Å. Each compound contains a bulky protecting group (di-methyl-amino-sulfon-yl) which can be easily removed under mildly acidic conditions.

Keywords: amide; azide; crystal structure; imidazole; nagelamide.

Grants and funding

This work was funded by Robert Welch Foundation grant 4Y-1362.