39633-00-6

Upstream product

• 1313434-83-1 (2E,3E)-dimethyl 2-((dimethylamino)methylene)-3-(2-oxo-2-phenylethylidene)succinate 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 67-56-1 methanol 
• 1006-65-1 3-phenylisoxazole 

Downstream Products

• 39632-97-8 7-phenyl-2,3-dihydropyrido[4,3-d]pyridazine-1,4-dione 

Relevant academic research and scientific papers

The synthesis of 7-substituted-2, 3-dihydropyrido [4, 3-d]pyridazine-1, 4-diones and 1, 4-Dioxo-7-substituted-1, 2, 3, 4-tetrahydropyrido[4, 3-d]pyridazine 6-oxides from methyl ketones

A general four-step transformation of alkyl, cycloalkyl, aryl, and heteroaryl methyl ketones via 3-(dimethylamino)-1-substituted-prop-2-en-1-ones, followed by microwave [2+2] cycloaddition of dimethyl acetylenedicarboxylate, cyclization of (2E, 3E)-2-[(dimethylamino)methylene]-3-(2-substituted)succinates with ammonia or hydroxylamine hydrochloride into 2-substituted-pyridine-4, 5-dicarboxylates and their N-oxides and final cyclization with hydrazine hydrate into of 7-substituted-2, 3-dihydropyrido[3, 4-d]pyridazine-1, 4-diones and 1, 4-dioxo-7-substituted-1, 2, 3, 4-tetrahydropyrido[ 4, 3-d]pyridazine 6-oxides is shown.

A simple metal-free synthesis of 2-substituted pyridine-4,5-dicarboxylates and their N-oxides

Herein a simple, metal-free synthesis of 2-alkyl-, 2-cycloalkyl-, 2-aryl-, and 2-heteroaryl-substituted pyridine 3,4-dicarboxylates and their N-oxides from the corresponding methyl ketones in good to excellent yield, demonstrated with 22 examples in each case, is described. The method complements the current coupling reactions of 2-heterocyclic organometallic reagents.

Novel pyridine-formation reactions of 2-(phosphoranylideneamino)acrylaldehydes with acetylenic esters. Synthesis of 2-mono-and 2,5-disubstituted nicotinates

Preparation of 2-(phosphoranylideneamino)acrylaldehydes, novel formyl-substituted (vinylimino)phosphoranes, was accomplished by the reaction of formyl-2H-azirines with triphenylphosphine. Their novel pyridine-formation reactions with acetylenic esters ach

Hexacarbonylmolybdenum-induced Reaction of Isoxazoles. Cycloaddition of Isoxazoles with Acetylenic Esters and Related Reactions

In the presence of hexacarbonylmolybdenum, substituted isoxazoles undergo a cycloaddition reaction with dimethyl acetylenedicarboxylate across the C-4-C-5 bond to give 3,4-bis(methoxycarbonyl)pyridine derivatives.In a similar cycloadition of isoxazoles with methyl propiolate, 4-(methoxycarbonyl)pyridine derivatives were also obtained.The β-carbon atom of methyl propiolate could intervene in the bonding with the C-5 position of the isoxazoles regioselectively.A mechanism involving a complexed 2-oxa-3-azabicyclohepta-3,6-diene derivative and the subsequent N-Oand C-1-C-5 bond cleavage leading to a complexed (β-ketovinyl)nitrene intermediate is proposed for the formation of pyridine derivatives.In order to clarify the mechanistic aspect, the reaction of 4-phenyl-2-oxa-3-azabicyclohepta-3,6-diene and its related compounds were also studied to give pyridine derivatives.

HEXACARBONYLMOLYBDENIUM-INDUCED FORMATION OF PYRIDINES FROM ISOXAZOLES AND ACETYLENIC ESTER

Upon treatment with Mo(CO)6 in anhydrous benzene, substituted isoxazoles undergo a novel inclusion of dimethyl acetylenedicarboxylate across the C4-C5 bond and loss of an oxygen atom to lead to pyridines.