D. G. Kim

A single crystal X-ray study of the products of halogen mercury cyclization of 8-allylthioquinoline

The reaction products of 8-allylthioquinoline with mercury halides are studied by single crystal X-ray diffraction. It is shown that the products are organomercury derivatives of salts of 2,3-dihydro[1,4]-thiazino[2,3,4-ij]quinoliniuim.

Alkenyl derivatives of 5-nitro-2-pyridone: Synthesis and halocyclization

Alkylation of 5-nitro-2-pyridone by alkenyl halides in acetone in the presence of K2СО3 proceeds with generation of a mixture of N- and О-derivatives with N-isomer prevailing. 1-Allyl- and 1-methylallyl-5-nitro-2-pyridone react with halogens with the formation of 2-halomethyl-6-nitro-2,3-dihydrooxazolo[3,2-a]-pyridinium halides. 1-Prenyl-5-nitro-2-pyridone reacts with bromine with the formation of 3-bromine-2,2-dimethyl-7-nitro-3,4-dihydro-2Н-pyrido[2,1-b][1,3]oxazinium bromide, and with iodine giving 2,2-dimethyl-7-nitro-3,4-dihydro-2Н-pyrido[2,1-b][1,3]oxazinium triiodide.

Synthesis and iodination of 2-(alkenylsulfanyl)quinolines

Abstract2-(2-Methylprop-2-en-1-ylsulfanyl)quinoline and 2-(3-methylbut-2-en-1-ylsulfanyl)quinolines reacted with iodine to give dihydrothiazolo[3,2-a]quinolinium polyiodides, whereas iodination of 2-(but-3-en- 1-ylsulfanyl)quinoline afforded dihydro[1,3]thiazino[3,2-a]quinolinium polyiodide.

Halocyclization of S- and N-alkenyl derivatives of 5-methyl-1,3,4-thiadiazole-2-thione

2-Allylsulfanyl-5-methyl-1,3,4-thiadiazole, 2-(2-bromoallylsulfanyl)-5-methyl-1,3,4-thiadiazole, 2-[(but-3-en-1-yl)sulfanyl]-5-methyl-1,3,4-thiadiazole, and 2-methyl-5-[(pent-4-en-1-yl)sulfanyl]-1,3,4-thiadiazole were obtained by alkylation of 5-methyl-1,3,4-thiadiazole-2-thione. Halocyclization of the obtained unsaturated sulfides produced derivatives of thiazolo[2,3-b][1,3,4]thiadiazolium, 6,7-dihydro-5H-[1,3,4]-thiadiazolo[2,3-b][1,3]thiazinium, and 5,6,7,8-tetrahydro[1,3,4]thiadiazolo[2,3-b][1,3]thiazepinium systems.

Synthesis of oxazolo[3,2-a]quinolinium triiodide from 4-methyl-1-(3-methylbut-2-enyl)quinolin-2(1H)-one

It is known [1, 2] that the S-prenyl derivatives of heterocycles react with halogens to form six-membered rings and this relates to an electrophilic attack on the -carbon atom. We have found that the reaction of 4-methyl-1-(3-methylbut-2-enyl)quinolin-2(1H)-one (1) with iodine occurs with an electrophilic attack of halogen at the terminal -carbon atom of the double bond to yield 2-(1-iodo-1-methylethyl)-5-methyl-1,2-dihydro[1,3]oxazolo[3,2-a]quinolinium triiodide (2). Compound 1 was prepared by the reaction of 4-methylquinolin-2(1H)-one with 1-bromo-3-methylbut2-ene in 2-PrOH in the presence of alkali.

Heterocyclization of 2-(Propargylsulfanyl)-1,3-thiazole Derivatives by the Action of Halogens

Reactions of 2-(propargylsulfanyl)-5-methyl-1,3,4-thiadiazole, N-[5-(propargylsulfanyl)-1,3,4-thiadiazol- 2-yl]benzamide, 2-(propargylsulfanyl)-1,3-benzothiazole, and 2-(propargylsulfanyl)-4,5-dihydro-1,3- thiazole with iodine involved annulation of the unsaturated substituent with formation of fused thiazole ring. 2(5)-(Propargylsulfanyl)-1,3,4-thiadiazole derivatives reacted with bromine to give mixtures of heterocyclization products and bromine adducts to the triple bond. The bromination of 2-(propargylsulfanyl)-4,5-dihydro- 1,3-thiazole afforded only the bromine addition product to the triple bond.

Halocyclization of 1-Allyl-6(7)-methylquinolin-2(1H)-ones

Oxidation of 1-allyl-6- and -7-methylquinolinium iodides with potassium hexacyanoferrate(III) gave 1-allyl-6(7)-methylquinolin-2(1H)-ones which reacted with halogens to afford 2-halomethyl-7(8)- methyl-1,2-dihydro[1,3]oxazolo[3,2-a]quinolinium halides.

Synthesis of Fused Thiazolo- and Thiazinopurine Ring Systems Containing a 6-Thiopurine Moiety

This short review provides a general and systematic coverage of literature published since 1961 on the synthesis of [1,3]thiazolo[2,3-i]-, [1,3]thiazino[2,3-i]-, [1,3]thiazolo[3,4,5-gh]-, [1,4]thiazino[4,3,2-gh]purine systems and their hydrogenated derivatives.

Halocyclization of 2-allyl(propargyl)sulfanyl-6-aminopyrimidin-4(3H)-ones

The alkylation of 6-amino-2-thiouracil with allyl, methallyl, and propargyl halides in the presence of bases gave 2-[allyl(methallyl, propargyl)sulfanyl]-6-aminopyrimidin-4(3H)-ones which reacted with iodine and bromine to form fused [1,3]thiazolo[3,2-a]pyrimidinium systems. Their nitrosation with sodium nitrite in acid medium afforded 2-[allyl(propargyl)sulfanyl]-6-amino-5-nitrosopyrimidin-4(3H)-ones.

Synthesis of 2-(halomethyl)-3,4-dihydro-2 H -pyrido[2,1- b ][1,3]oxazinium halides

Alkylation of pyridin-2(1H)-one and 5-nitropyridin-2(1H)-one with 4-bromobut-1-ene afforded a mixture of N- and O-butenyl derivatives. 1-(But-3-en-1yl)pyridin-2(1H)-one and 1-(but-3-en-1-yl)-5-nitropyridin- 2(1H)-one reacted with bromine and iodine to give 2-(halomethyl)-3,4-dihydro-2H-pyrido[2,1-b][1,3]-oxazinium halides.