Advances in Heterocyclic Chemistry, Vol. 70 by Alan R. Katritzky

By Alan R. Katritzky

Verified in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area--one of serious value to natural chemists, polymer chemists, and lots of organic scientists. Written via proven experts within the box, the great experiences mix descriptive chemistry and mechanistic perception and yield an realizing of ways the chemistry drives the homes.

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Ring Opening The presence of a substituent at position 1 of perhydropyrido[l,2c][l,3]oxazines decreases the stability of the bicycle (54JA2431). Hydrolysis of perhydropyrido[ 1,2-~][1,3]oxazines [56CLY1180; 57CLY927; 60JOC2028;70LA(737)24] or their 1-0x0 derivatives (84JA3240;91TL4371; 93JA8851) gave 2-(2-hydroxyethyl)piperidines, whereas that of pyrido[3,2,1-ij][3,l]benzoxazin-3-ones and the -1,3-dione yielded 8-hydroxymethyl-1,2,3,4-tetrahydroquinolines (87EUP239129; 90CPB1575) and 1,2, 3,4-tetrahydroquinoline-8-carboxylic acid (64M59), respectively.

The reaction of 2-cyanomethylperhydropyrimidine with LAH gave the 2-(2-aminoethyl) derivative (69JHC181). 52 ISTVAN HERMECZ [Sec. C 6. Ring Transformation 8-Cyano-1,2,3,4-tetrahydro-6H,7H-1,6-naphthyridin-7-one was obtained from 127 in boiling water (80KGS416,80KGS1120) or by heating in DMF in the presence of benzylamine (82KGS518). Treatment of 2-benzyl-9chloro-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinazolin-7-onewith NaN3 in chloroform in the presence of concentrated H2S04 gave 2-benzyl-10chloro-1,2,3,5,6,7-hexahydro-8H-pyrimido[5,6,1-jk][1,4]benzodiazepin-8one (72MI1).

9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido[6,1-a] Reaction of isoquinoline-2,4-diones (84JMC1470) and 2-[2-(l-pyrrolidinyl)ethyl]2,3,4,4a,5,6-hexahydro-lH-pyrimido[l,6-a]quinolin-l-one (7OUSP3494922) with P&o gave the 2-thioxo and 1-thioxo derivatives, respectively. (In the first case the products were earlier described as 2-0x0-4-thioxo derivatives [77SAP77/06706; 78GEP2720085; 79GEP28012891. Treatment of trequinsin (19)with dimsyl ion gave the ring-opened product 114 when a short reaction period (5 min) was applied, but a longer reaction period led to a mixture of 115 and 114 (reaction period 15 min), or a mixture of 116 and 115 (reaction period 45 min) (90JOC5117).

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