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By Alan R. Katritzky

Proven in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area--one of serious significance to natural chemists, polymer chemists, and plenty of organic scientists. Written via validated professionals within the box, the great stories mix descriptive chemistry and mechanistic perception and yield an knowing of the way the chemistry drives the homes.

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B ISTVAN HERMECZ \ I / ob . (aMe O Y O EtOOCCH2CN. NaOH, dioxane, A \ n=O 58% DMe I NaH 120 C, ca. 5 h 36% SCHEME14 2. Reactivity of Rings The reaction of 1,3,4,4~,5,10-hexahydro~l,3]thiazino[3,4-b]isoquinolinel-thione and methyl iodide gave l-methylthio-4,4~,5,1O-tetrahydro-3H[1,3]thiazino[3,4-b]isoquinoliniumiodide, which reacted with 5-aminoisoquinoline in pyridine at 40°C to afford l-(5-isoquinolylirnino)-1,3,4,4~,5, l0-hexahydro[l,3]thiazino[3,4-b]isoquinoline(79GEP2848926). Sec. C] PYRIDO[1,2-c][1,3]OXAZINES, -THIAZINES, & -PYRIMIDINES, I1 41 The 4-(substituted imino) moiety of 1,2,4,6,7,11b-hexahydro-2H-[l,3]thiazino[4,3-~]isoquinolineswas substituted with another (substituted imino) group when 9,10-dimethoxy-l-hydroxymethyl-4-(substituted imino)-1,2,4, 6,7,llb-hexahydro-[l,3]thiazino[4,3-a]isoquinolines were reacted with primary amines in boiling ethanol (85GEP3510526).

The hydroxy groups of 9-methoxy-10-hydroxy- and 9-hydroxy-10met hoxy-3-met hy l-Z(N-mesi tylimino)-2,3,6,7-tetra hydro-4H-pyrirnido[6,1- 50 ISTVAN HERMECZ [Sec. C a]isoquinolin-4-oneswere alkylated with epibromohydrin to give 3’-bromo2’-hydroxypropyl (84INIP153028) or 2 ‘,3’-epoxypropoxy derivatives (83EUP75165). The epoxy and bromo derivatives were reacted with amines (83EUP75165; 84INIP153028). The side-chain hydroxy group of 3-(2hydroxye thyl)-9,10-dimethoxy-1,3,4,5,6,1lb-hex ahyd ro-2H-py rimi do[6,1a]isoquinolin-2-one was acylated with acyl chlorides (61JMC505; 62USP3021331).

In the case of the pyrimid0[6,1-~]isoquinolinederivative, the starting compounds were earlier described as 4-thioxo-2-0x0 derivatives [77SAP77/ 06706; 78GEP2720085; 79GEP28012891. 1,9-Diazacycl[3,3,3]azines(125 and 126) were prepared by the reaction of 1-imino-8-methyl-1H-pyrido[l,2-c]pyrimidines (124)with ethoxymethylenemalononitrile and acetic anhydride, respectively (74CPB2765; 78YZ623). In the latter cases, the hydrolysis of the imino group also occurred to give 4-0x0 derivatives of 124 (78YZ623).

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