The formation of an unexpected heterocyclic scaffold, a benzoxazole, in a three-component reaction between a ketone, isocyanide, and 2-aminophenol was encountered. This reaction involved a benzo[b][1,4]oxazine intermediate resulting from intramolecular attack of the aminophenol hydroxyl group on the nitrilium ion. Unlike previous literature examples, the trapped nitrilium benzo[b][1,4]oxazine c...

The title fluorinated bis-benzoxazine, C18H18F2N2O2, crystallizes with one half-mol-ecule in the asymmetric unit, which is completed by inversion symmetry. The fused oxazine ring adopts an approximately half-chair conformation. The two benzoxazine rings are oriented anti to one another around the central C-C bond. The dominant inter-molecular inter-action in the crystal structure is a C-H⋯F hyd...

The total synthesis of (+)-nakadomarin A is described. A three-component cycloaddition of a hydroxylamine, aldehyde, and cyclopropane to form a highly functionalized tetrahydro-1,2-oxazine serves as the foundation for this synthesis. The resulting oxazine is formed as a single diastereomer with the absolute configuration being dictated by the chirality of the cyclopropane. Other key steps inclu...

Here we present the first pyrimido-pyrrolo-oxazine-based mTOR kinase inhibitor (11) predicted to penetrate blood brain barrier (BBB). Thus, 11 has a potential in treatments of neurological disorders.

One of the most important goals in medicinal chemistry is the development of new techniques and new heterocyclic compounds with pharmaceutical activity. The present study aimed to use a method for the synthesis of some 1,2-Dihydro-1-arylnaphtho [1,2-e] [1,3] oxazine-3-ones. The question this study tried to answer was this reaction can be performed in present of nano-Fe2O3 as an acid catalyst an...

A new alkaloid, 2-(furan-2-yl)-6-(2S,3S,4-trihydroxybutyl)pyrazine (1), along with 12 known compounds, 2-(furan-2-yl)-5-(2S,3S,4-trihydroxybutyl)pyrazine (2), (S)-4-isobutyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (3), (S)-4-isopropyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (4), (4S)-4-(2-methylbutyl)-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-...

Examination of the product of affinity labeling of delta 5-3-ketosteroid isomerase (EC 5.3.3.1) of Pseudomonas testosteroni by the suicide substrate [7-3H]5,10-secoestr-5-yne-3,10,17-trione has demonstrated that the steroid becomes bound by an acid- and base-labile linkage to an active-site peptide representing residues 55-58 (H2N-Tyr-Ala-Asn-Ser-CO2H) of the primary structure (Penning, T. M., ...

Oxazine derivatives are an important class of heterocycles, which has attracted much synthetic interest due to their wide range of biological activities. Oxazine is a heterocyclic compound can be formally derived from benzene, and its reduction products, by suitable substitution of carbon (and hydrogen) atoms by nitrogen and oxygen. In the last few years oxazine derivatives have proved to be va...

This study has provided a rational approach for the development of new 3,4-dihydro-2H-benzo[1,4]oxazine derivatives as potential 5-HT6 antagonists. The descriptors identified in CP-MLR analysis have highlighted the role of atomic van der Waals volume in terms of BEHv6, path/walk ratio 3 and 4Randic shape index (PW3 and PW4), number of rotatable bonds (RBN) and superpendentic index (SPI) to expl...

A concise, stereocontrolled synthesis of (+)-polyoxamic acid was achieved. Starting from trans-oxazoline as a chiral building block, the key step involves diastereoselective oxazine formation catalyzed by palladium(0).