57492-84-9

Upstream product

• 69813-73-6 N-<4-ethyl-(2-methyl-6,7-methylenedioxy-4-quinazolinylmethyl)-phenyl>carbamate 
• 85591-06-6 4-[Acetyl-(6-methyl-[1,3]dioxolo[4,5-g]quinazolin-8-ylmethyl)-amino]-benzoic acid ethyl ester 
• 66117-65-5 7-benzoylamino-6,8-dimethyl-[1,3]dioxolo[4,5-g]quinazolinium betaine 
• 109-73-9 N-butylamine 
• 57492-79-2 N-(2,4-dimethyl-6,7-methylenedioxy-3-quinazolinio)-ethoxyformamidate 
• 67-64-1 acetone 

Downstream Products

• 106391-38-2 2,4,6-Trimethyl-benzenesulfonate5-amino-6,8-dimethyl-[1,3]dioxolo[4,5-g]quinazolin-5-ium; 

Relevant academic research and scientific papers

Electron Deficient Heteroaromatic Ammonioamidates. Part 24. N-(Quinazolin-3-io)amidates. Part 11. The Photochemistry of N-(6,7-Methylenedioxyquinazolin-3-io)amidates in Acetone

N-(Quinazolin-3-io)amidates (1) may exist, depending on the nature of the groups R, R1, and R2, and in the absence of nucleophiles, as equilibrium mixtures of the monomeric (1) and dimeric (3) forms.For the first time evidence has been found for the generation of photoproducts of the dimeric forms (3) via irradiation of the quinazolinioamidates (1a-c) in acetone in which substantial amounts of the dimers (3a-c) are present.Thus, the quinazolinioamidates (1) are the only heteroaromatic ammonioamidates which are known not only to exist in three forms, viz. the monomer, the adducts (2), and the dimers (3), but also to furnish characteristic photoproducts of all three forms.

THE SYNTHESIS OF SOME COMPLEX QUINAZOLINE DERIVATIVES CONTAINING ONE OR TWO QUINAZOLINE RINGS AND CARRYING AMINO, ACYLAMINO, ESTER AND/OR CARBAMATE FUNCTIONAL GROUPS IN THEIR SIDE CHAINS

The scope of the Bischler synthesis has been extented to the synthesis of complex quinazoline derivatives 3b-3d, 5a-5f, 6a, 6b, 7 and 8.Reductive cleavage of the C-N bond of all 4-(N-monosubstituted aminomethyl)quinazolines tested took place on treatment with ethanol in the presence of acids or bases.

ELECTRON DEFICIENT HETEROAROMATIC AMMONIOAMIDATES, PART 22. N-(3-QUINAZOLINIO)AMIDATES, PART 10. Thermolysis of N-(2,4-dimethyl-6,7-methylenedioxy-3-quinazolinio)ethoxyformamidate and of ethyl N-(2-methyl-4-methylene-6,7-methylenedioxy-3,4-dihydro-3-quinazolinyl)-N-phenylcarbamate.

N-(2,4-Dimethyl-6,7-methylenedioxy-3-quinazolinio)ethoxyformamidate (1b), upon prolonged refluxing in dioxane, furnished mixtures of the quinazoline derivatives 3b, 4, 5 and 6, and ethyl carbamate; in butanol compound 4 was formed as the sole thermolysis product.N-(2-Methyl-4-methylene-6,7-methylenedioxy-3,4-dihydro-3-quinazolinyl)-N-phenylcarbamate (2c) was transformed on refluxing in dioxane into mixtures of its two isomers 3c and 7.Possible modes of formation of these products are discussed, and the results of the thermolyses are compared with those of the photolyses of compounds 1b and 2c described earlier.

ELECTRON DEFICIENT HETEROAROMATIC AMMONIOAMIDATES, XIX. N-(3-QUINAZOLINIO)AMIDATES, VII. THE PHOTOCHEMISTRY OF N-(3-QUINAZOLINIO)AMIDATES IN THE PRESENCE OF AMINES AND OF ACETAMIDE

Irradiation by Pyrex-filtered light of the quinazolinioamidates 1c-1f and of the dimers 2a and 2b in butylamine, of compound 2b in benzylamine and morpholine, and in the presence of acetamide in dioxane or dichloromethane, as well as of the adducts 5a and 5b in dichloromethane leads to complex mixtures of Type 6-16 products.While the compounds 6-9 are the products of Type II cleavage processes of the Type 3-5 adducts, the parent quinazolines 12 are formed from the amidates 1 themselves, amides 14 being the co-products in both cases.Compound 10a is formed by deacetylation of 9a during work-up, while compound 11b is a secondary photosubstitution product of 12b by the solvent dioxane.At least part of the compounds 13, 15 and 16 is the result of dark reactions.