Formation of Hydro-1,3-diazines by the Reaction of Benzo[b]cyclohepta[e][1,4]oxazine with α,γ-Diamines

Sato, Ohki; Seshimo, Manabu; Tsunetsugu, Josuke

doi:10.1039/a707825k

Cited by 7 publications

(4 citation statements)

References 9 publications

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“…The organic layer was concentrated, and the residue was purified by aluminum oxide (basic) chromatography (methanol/CH 2 Cl 2 /hexane, gradient from 0:4:6 to 1:3:6). 2-Phenyl-1,4,5,6-tetrahydropyrimidine ( 13 ): compound 13 , was obtained as a white solid (90 mg, 79%) recrystallized from ethyl acetate. The 1 H NMR was identical to that in the literature; mp 98–99 °C (lit .…”

Section: Methodsmentioning

confidence: 99%

“…2-Phenyl-1,4,5,6-tetrahydropyrimidine ( 13 ): compound 13 , was obtained as a white solid (90 mg, 79%) recrystallized from ethyl acetate. The 1 H NMR was identical to that in the literature; mp 98–99 °C (lit . mp 88–91 °C).…”

Section: Methodsmentioning

confidence: 99%

“…Much more promising results were obtained with the solution phase reagent 1 . Thus, when the amide 6 was treated with 1 equiv of reagent 1 and DIPEA in dry DCM (Scheme ), the desired cyclic amidine 13 , was isolated in 36% yield following an aqueous workup (the triphenylphosphine oxide byproduct remains in the organic layer) and chromatography on basic alumina.…”

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confidence: 99%

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Cyclodehydration of N-(Aminoalkyl)benzamides under Mild Conditions with a Hendrickson Reagent Analogue

2013

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Methods for the cyclodehydration of N-(aminoalkyl)benzamides are few and employ harsh reaction conditions. We have found that the easily prepared phosphonium anhydrides 1 (Hendrickson reagent) or 2 can be used for cyclodehydration of N-(aminoalkyl)benzamides under very mild conditions (room temperature) to produce five-, six-, and seven-membered cyclic amidines. Good yields are obtained by employing a temporary trityl group protection strategy. Cyclic analogue 2 can be used when the product cyclic amidine is organic-soluble, thus producing water-soluble byproducts.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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confidence: 99%

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Cyclodehydration of N-(Aminoalkyl)benzamides under Mild Conditions with a Hendrickson Reagent Analogue

2013

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“…Due to their nonequivalence the signals for the C-6 methylene protons in compounds 5-7 appear as a double doublet with a geminal spin-spin coupling of 2 J = 13.4-14.0 Hz. The 1 H and 13 C NMR spectra of the tetrahydropyrimidines 5-7 show only one set of signals and this can be due either to a rapid prototropic tautomeric process on the NMR time scale [19] or to a fixed position of the proton at the N-5 atom. A second set of proton signals for the C-2 and C-6 atoms in CD 3 OD was not seen even at -60ºC and this suggests that only one of the possible isomers is formed.…”

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confidence: 98%

Synthesis of norbornane series tetra- and hexahydropyrimidines

Shafikova

Петров

Sapozhnikova

et al. 2009

Chem Heterocycl Comp

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Pyrimidine derivatives attract the attention of synthetic chemists and of pharmacologists thanks to their unique properties of low toxicity and broad spectrum of physiological activity (analgesic, immunotropic, anti-inflammatory, antiviral, hepatoprotective, antioxidant, and antiradical) [1-7]. Many compounds used in medical practice are close analogs of pyrimidine nucleosides. Work on the synthesis of novel compounds amongst this class is very actively pursued [8][9][10][11]. It is known that pyrrolidinones containing a condensed norbornane fragment have antiarrhythmic properties and norbornane series amines and their acyl derivatives show neurotropic, anti-inflammatory, antiglycemic, and other types of activity [12][13][14][15]. There is, however, no information in the literature regarding the synthesis and properties of norbornanes containing condensed exoorientated tetra-and hexahydropyrimidine structures at the 2, 3 position of the norbornane ring.This report concerns the targeted synthesis of 3,5-diazatricyclo[6.2.1.0 2,7 ]undecanes containing tetraand hexahydropyrimidine fragments in an exo position to a norbornane structure through study of the condensation reaction of exo-2-amino-exo-3-aminomethylnorbornane (1) with formaldehyde, acetaldehyde, benzaldehyde, salicylaldehyde, acetone, methylcyclopropyl ketone, cyclohexanone, and urea and with formic, acetic, and benzoic acids.The reaction of diamine 1 with an equimolar amount of formaldehyde, acetaldehyde, benzaldehyde, or salicylaldehyde occurs at room temperature with heating of the reaction mass and gives a hard to separate mixture of condensation products.

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ChemInform Abstract: Formation of Hydro‐1,3‐diazines by the Reaction of Benzo[b]cyclohepta[e][1,4]oxazine with α,γ‐Diamines.

1999

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Formation of Hydro-1,3-diazines by the Reaction of Benzo[b]cyclohepta[e][1,4]oxazine with α,γ-Diamines

Cited by 7 publications

References 9 publications

Cyclodehydration of N-(Aminoalkyl)benzamides under Mild Conditions with a Hendrickson Reagent Analogue

Cyclodehydration of N-(Aminoalkyl)benzamides under Mild Conditions with a Hendrickson Reagent Analogue

Synthesis of norbornane series tetra- and hexahydropyrimidines

ChemInform Abstract: Formation of Hydro‐1,3‐diazines by the Reaction of Benzo[b]cyclohepta[e][1,4]oxazine with α,γ‐Diamines.

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