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Synthesis of 1,4-dihydro-benzo[d][1,3]oxazin-2-ones from phthalides via an aminolysis-Hofmann rearrangement protocol.

ABSTRACT: A simple two-step procedure for the conversion of readily available phthalides to the corresponding benzoxazinones was developed. Initial ring-opening aminolysis to form a primary 2-hydroxymethylbenzamide, followed by reaction with bis(trifluoroacetoxy)iodobenzene (BTI) conveniently provided a variety of 4-substituted benzoxazinones.

SUBMITTER: Hernandez E

PROVIDER: S-EPMC2194645 | biostudies-literature | 2007 Dec

REPOSITORIES: biostudies-literature

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Synthesis of 1,4-dihydro-benzo[d][1,3]oxazin-2-ones from phthalides via an aminolysis-Hofmann rearrangement protocol.

Hernández Eliud E Vélez Jessica M JM Vlaar Cornelis P CP

Tetrahedron letters 20071201 51

A simple two-step procedure for the conversion of readily available phthalides to the corresponding benzoxazinones was developed. Initial ring-opening aminolysis to form a primary 2-hydroxymethylbenzamide, followed by reaction with bis(trifluoroacetoxy)iodobenzene (BTI) conveniently provided a variety of 4-substituted benzoxazinones. ...[more]

PMID: 19096499

Similar Datasets

4H-Benzo[d][1,3]oxazin-4-ones and Dihydro Analogs from Substituted Anthranilic Acids and Orthoesters.

Project description:A one-pot route to 2-alkyl and 2-aryl-4H-benzo[d][1,3]oxazin-4-ones (also known as 4H-3,1-benzoxazin-4-ones) has been developed and studied. The method involves the reaction of aryl-substituted anthranilic acids with orthoesters in ethanol catalyzed by acetic acid. Additionally, we have also investigated the reaction under microwave conditions. Not all of the substrates were successful in yielding the target heterocycles as some of the reactions failed to undergo the final elimination. This process led to the isolation of (±)-2-alkyl/aryl-2-ethoxy-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-ones. The formation of the dihydro analogs correlated with the electron density on the aromatic ring: Electron-donating groups favored the 4H- benzo[d][1,3]oxazin-4-ones, while electron-withdrawing groups tended to favor the dihydro product. Substituting a pyridine ring for the benzene ring in the substrate acid suppressed the reaction.

| S-EPMC6804250 | biostudies-literature

Regiospecific Synthesis and Structural Studies of 3,5-Dihydro-4H-pyrido[2,3-b][1,4]diazepin-4-ones and Comparison with 1,3-Dihydro-2H-benzo[b][1,4]diazepin-2-ones.

Project description:Nine 3,5-dihydro-4H-pyrido[2,3-b][1,4]diazepin-4-ones (17-25), some of which contain fluoro-substituents, have been regiospecifically prepared by reaction of 2,3-diaminopyridines with ethyl aroylacetates. In two cases, open intermediates have been isolated and these are related to the reaction pathway. The X-ray crystal structure of 1-methyl-4-phenyl-3,5-dihydro-4H-pyrido[2,3-b][1,4]diazepin-4-one (23) has been solved (formula, C15H13N3O; crystal system, monoclinic; space group, C2/c). This is an asymmetric unit constituted by a single nonplanar molecule and its conformational enantiomer due to the presence of the seven-membered diazepin-2-one moiety, which introduces a certain degree of torsion in the adjacent pyridine ring. The 1H, 13C, 15N, and 19F NMR spectra were obtained and the chemical shifts, together with those of the previously published 1,3-dihydro-2H-benzo[b][1,4]diazepin-2-ones (1-16), i.e., a total of 544 values, were successfully compared with the chemical shifts calculated at the gauge invariant atomic orbital (GIAO)/Becke, three-parameter, Lee-Yang-Parr (B3LYP)/6-311++G(d,p) level. The seven-membered ring inversion barrier in 5-benzyl-2-phenyl-3,5-dihydro-4H-pyrido[2,3-b][1,4]diazepin-4-one (25) was determined and, in conjunction with the data from the literature, compared with the B3LYP/6-311++G(d,p) computed values. This allowed the determination of several structural effects. The rotation about the exocyclic N1-CR bond was also calculated and its dynamic properties were discussed.

| S-EPMC7542844 | biostudies-literature

4-Oxo-1,4-dihydro-benzo[h][1,3]thia-zeto[3,2-a]quinoline-1,3-dicarb-oxy-lic acid.

Project description:In the title mol-ecule, C(16)H(9)NO(5)S, there is an intra-molecular O-H⋯O hydrogen bond involving the quinolone carbonyl O atom and a carboxyl OH group. In the crystal, inter-molecular O-H⋯O hydrogen bonds between the carbonyl group of the quinolone carboxyl group, and a second carboxyl group on the thia-zeto moiety lead to the formation of chains propagating along [201] and perpendicular to the π-stacks of mol-ecules.

| S-EPMC3051750 | biostudies-literature

Structure-Guided Design of C4-alkyl-1,4-dihydro-2H-pyrimido[4,5-d][1,3]oxazin-2-ones as Potent and Mutant-Selective Epidermal Growth Factor Receptor (EGFR) L858R/T790M Inhibitors.

Project description:Epidermal growth factor receptor (EGFR) T790M acquired drug-resistance mutation has become a major clinical challenge for the therapy of non-small cell lung cancer. Here, we applied a structure-guided approach on the basis of the previous reported EGFR inhibitor (compound 9), and designed a series of C4-alkyl-1,4-dihydro-2H-pyrimido[4,5-d][1,3]oxazin-2-one derivatives as novel mutant-selective EGFR inhibitors. Finally, the most representative compound 20a was identified, which showed high selectivity at both enzymatic and cellular levels against EGFRL858R/T790M (H1975 cell lines) over EGFRWT (A431 cell lines). The representative compound 20a also showed promising antitumor efficiency in the in vivo antitumor efficacy study of H1975 xenograft mouse model driven by EGFRL858R/T790M. These results provide a new scaffold for the treatment of dual-mutant-driven non-small cell lung cancer.

| S-EPMC5476563 | biostudies-literature

1,4-Dihydro-benzo[g]quinoxaline-2,3-dione.

Project description:The title compound, C12H8N2O2, was prepared by the reaction of the diethyl ester of naphthalene-bis-(oxamate) with tert-BuNH2. The mol-ecule is nearly planar, with an r.m.s. deviation of 0.017?Å from the plane through all 16 non-H atoms. In the crystal, a three-dimensional network is formed, composed of layers of mol-ecules along the b- and c-axis directions, due to the formation of inter-molecular N-H?O hydrogen bonds, as well as of chains along the a-axis direction due to parallel displaced sandwich-type ?-? inter-actions with average distances between the inter-acting mol-ecules in the range 3.35-3.40?Å.

| S-EPMC3589036 | biostudies-literature

Microwave assisted regioselective halogenation of benzo[b][1,4]oxazin-2-ones via sp2 C-H functionalization.

Project description:A microwave assisted, palladium-catalyzed regioselective halogenation of 3-phenyl-2H-benzo[b][1,4]oxazin-2-ones has been demonstrated using inexpensive and readily available N-halosuccinimide. The reaction utilizes the nitrogen atom present in the heterocyclic ring as the directing group to afford regioselective halogenated products in good to moderate yields. The established protocol provides wide substrate scope, high functional group tolerance, and high atom and step economy. The reaction proved to be cost-effective and time-saving as it required only a few minutes for completion and is amenable to gram scale. The halogen atoms present in synthesized products provide further scope for post-functionalization. Several post-functionalized products have also been synthesised to demonstrate the high utility of the reaction in the field of drug discovery and late-stage functionalization.

| S-EPMC9841512 | biostudies-literature

Formation of 2-Imino Benzo[e]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic Studies.

Project description:We describe a new 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU)-mediated coupling reaction to produce 2-imino benzo[e]-1,3-oxazin-4-ones from salicylic acids and anilines. Mechanistic studies support a reaction pathway in which HATU mediates carbon transfer to the initially formed salicylanilides to form in succession reactive tetramethylisouronium and N-acyl(dimethyl)isouronium intermediates, which then undergo imine-iminium exchange to generate the desired oxazinones.

| S-EPMC5793036 | biostudies-literature

Gold-catalyzed oxycyclization of allenic carbamates: expeditious synthesis of 1,3-oxazin-2-ones.

Project description:A combined experimental and computational study on regioselective gold-catalyzed synthetic routes to 1,3-oxazinan-2-ones (kinetically controlled products) and 1,3-oxazin-2-one derivatives (thermodynamically favored) from easily accessible allenic carbamates has been carried out.

| S-EPMC3678844 | biostudies-literature

2-Butyl-11-phenyl-5,10-dihydro-1H-benzo[e]imidazo[1,5-a][1,4]diazepine-1,3(2H)-dione.

Project description:The title compound, C(21)H(21)N(3)O(2), was obtained following a five-step synthetic procedure yielding weakly diffracting rod and needle-shaped crystals which crystallized concomitantly. Structural analysis of a rod-shaped crystal showed that the central seven-membered heterocyclic ring adopts a conformation that is perhaps best described as a distorted boat, with the H-bearing (CH(2) and NH) atoms lying well out of the least-squares mean plane fitted through the other five atoms in the ring (r.m.s. deviation 0.075 Å). In the crystal, the compound packs as a twisted chain, which propagates along the b axis by means of an R(1) (2)(6) motif formed by one of the carbonyl O atoms acting as a bifurcated acceptor in an N-H⋯O and C-H⋯O inter-action. No diffraction was observed from the needle-shaped crystals.

| S-EPMC2983587 | biostudies-literature

1-(6-Bromo-3,4-dihydro-2H-1,4-benz-oxazin-4-yl)-2,2-dichloro-ethanone.

Project description:The title compound, C(10)H(8)BrCl(2)NO(2), is a target mol-ecule in our research on herbicide safeners. The oxazine ring has an envelope conformation, with puckering parameters close to ideal values [Q = 0.498 (3) Å, θ = 53.7 (3)° and ϕ = 253.4 (4)°]. The crystal structure is stabilized by C-H⋯O, C-H⋯Cl and C-H⋯Br inter-actions.

| S-EPMC3414960 | biostudies-literature

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