An Efficient Chemical Fixation of Nitric Oxide: Convenient and Practical Synthesis of 1,2,3‐Oxadiazole 3‐Oxides.

Abstract

An Efficient Chemical Fixation of Nitric Oxide: Convenient and Practical Synthesis of 1,2,3-Oxadiazole 3-Oxides. -Nitric oxide reacts efficiently with alkynyllithium at low temperature producing 1,2,3-oxadiazole 3-oxides, such as (II) and (IV). -(SUGIHARA*, T.; KUWAHARA, K.; WAKABAYASHI, A.; TAKAO, H.; IMAGAWA, H.; NISHIZAWA, M.; Chem. Commun. (Cambridge) 2004, 2, 216-217; Fac. Pharm. Sci., Tokushima Bunri Univ., Yamashiro, Tokushima 770, Japan; Eng.) -M. Paetzel 17-124

Oxadiazoles

“…Ab initio methods have also been used to calculate the geometry and the energy of 4,5-dihydro-1,2,3-oxadiazole (22): the molecule is predicted to be unstable, its most favorable mode of decomposition being a retro 1,3-dipolar addition to diazomethane and formaldehyde [28].…”

“…Several theoretical studies have addressed the structure and aromaticity of sydnones [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34]. Sydnones could be regarded as aromatic because their structures could be represented as cyclic arrays of p-orbitals containing six p-electrons, with four from the C¼NÀN system and two from the lone pair on oxygen.…”

“…A wide variety of 1,2,3-oxadiazole 3-oxides, valuable candidates for drug frameworks, have been synthesized by the reaction of nitric oxide with functionalized alkynyllithium derivatives [22]. A theoretical study [23] indicates that the overall reaction is stepwise and is considered to include two processes.…”

Functional Biosynthetic Stereodivergence in a Gene Cluster via a DihydrosydnoneN-oxide

“…31 Since then, only a few derivatives of this aromatic family were synthesised mostly using NO gas. [31][32][33][34][35][36] Notably, molsidomine containing a sydnone imine core has been approved as a vasodilating drug for angina pectoris. 37,38 Other similar heterocycles (Supplementary Table 1) including 4,5-dihydro-1,2,3-oxadiazole, 39 and 5-hydroxy-3-methyloxadiazolinium perchlorate have been synthesised.…”