4414-93-1

Upstream product

• 89968-51-4 10-(methoxyimino)phenanthren-9-one 
• 104-81-4 4-Methylbenzyl bromide 
• 14062-19-2 p-tolylacetic acid ethyl ester 
• 99894-35-6 10-(methoxyimino)phenanthren-9-one 
• 104-87-0 4-methyl-benzaldehyde 
• 115420-82-1 2,3-dihydro-2,2,2-triphenylphenanthro<9,10-d>-1,3,2λ⁵-oxazaphosphole 
• 84-11-7 9,10-phenanthrenequinone 
• 104-84-7 para-methylbenzylamine 
• 3942-85-6 10-imino-10H-phenanthren-9-one 
• 106-42-3 para-xylene 

Relevant academic research and scientific papers

The preparation of annulated 1,3-oxazoles from 1,3,2-oxazaphospholes and aldehydes

The reactions of 2,3-dihydro-2,2,2-triphenylphenanthro[9,10-d]-1,3,2-λ5-oxazaphospholes with aromatic aldehydes lead to the corresponding 2-substituted phenanthro[9,10-d][1,3]oxazoles via an aza-Wittig reaction in good yields.

A convenient strategy to 2,4,5-triaryl and 2-alkyl-4,5-diaryl oxazole derivatives through silver-mediated oxidative CO cross coupling/cyclization

This is a silver(I) mediated Cα(sp3)H activation of primary amines followed by oxidative CO cross coupling/cyclization for the construction of 2,4,5-triaryl and 2-alkyl-4,5-diaryl oxazole derivatives. The protocol has been successfully utilized to synthesize the oxazole derivatives in good to excellent yields. In this oxidative coupling, the silver species after the reaction was successfully re-synthesized and reused with almost a similar activity.

1,4-Benzoxazin-2-ones, benzo[d]oxazoles and 2H-1,4-benzoxazines from the reaction of 2-(methoxyimino)benzen-1-ones with arylacetates, arylacetic acids and trans-stilbene

10-(Methoxyimino)phenanthrene-9-one 1 reacts thermally with the arylacetic derivatives 2(a-j) to yield the corresponding 1,4-benzoxazin-2-ones 4(a-d,f) and benzo[d]oxazoles 5(a-e,g). Similarly, reaction of the monoximes 7a, 7b with compounds 2a, 2d respectively affords 8a, 8b, while action of trans-stilbene on the monoximes 1, 7a, 7b leads to the 1,4-benzoxazines 10, 11, 13, obtained along with the corresponding 2-phenyloxazoles 5a, 8a, 8c and compound 12.

Synthesis of Phenanthrooxazoles from 10-(Methoxyimino)phenantrene-9-one

10-(Methoxyimino)phenanthren-9-one 3 easily reacts with the methyl substituted aromatics 4(a-d), as well as with α-bromo-p-xylene 6 and the α-substituted methyl derivatives 7(a-i), to afford in 5-64percent yield the corresponding 2-aryl substituted phenanthrooxazoles 5(a-g), most probably via a free radical reaction sequence.In several cases the unsubstituted oxazole 12 is also obtained, while reaction of compound 3 with the N-methyl substituted amines 7g and 14(a,b) leads to the aminooxazoles 13 and 15(a,b) respectively.