New PDF release: Advances in Heterocyclic Chemistry, Vol. 70

By Alan R. Katritzky

ISBN-10: 0120207702

ISBN-13: 9780120207701

Proven in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area--one of significant value to natural chemists, polymer chemists, and plenty of organic scientists. Written through demonstrated professionals within the box, the great reports mix descriptive chemistry and mechanistic perception and yield an figuring out of ways the chemistry drives the houses.

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Additional info for Advances in Heterocyclic Chemistry, Vol. 70

Example text

The basic difference between the trans-fused and cis-fused conformations is that in the trans-fused ring conformations (Teq and Tax)the perhydropyrimidine ring is fused onto the tetrahydropyridine 28 ISTVAN HERMECZ N-inside cis-fused trans-f used 11 NZ inversion (59) 11 NZ inversion [Sec. C N-outside cis-fused li N* inversion Me cis-0, Tax I Me SCHEME10 ring, by utilization of the pseudoequatorial and equatorial bonds of the tetrahydropyridine ring, and this increases the strain in the fused system.

Reaction of 1-(nitromethylene)perhydropyrido[12-clpyrimidine with p chlorobenzenesulfonyl azide in dioxane at 80°C gave the tricyclic l-nitro6,6~,7,8,9,10-hexahydro-5H-pyrido[l,2-c] [1,2,3]thiazolo[l,5-u]pyrimidine [79JCS(P1)2361]. Sec. A] PYRIDO[1,2-c][1,3]OXAZINES, -THIAZINES, & -PYRIMIDINES, I1 53 IV. Synthesis A. PYRIDO[ 1,2-C] [1,3]0XAZINES AND THEIRBENZODERXVATIVES 1. By Formation of One Bond a to the Bridgehead Nitrogen Atom [6 +O ( 4 1 Treatment of 2-(2-~inyloxyethyl)pyridine with Br2 in CCl, at 0°C gave l-bromomethyl-2,3-dihydro-lH-pyrido[ 1,2-c][1,3]oxazinium bromide (86KGS1396).

The 4-methoxymethyl group was cleaved in 2 N hydrochloric acid to the hydroxymethyl group, which was oxidized with pyridinium chromate to the 4-aldehyde. The aldehyde was converted to its 4-oxime, which was dehydrated in refluxing Ac20, and the 4-nitrile was hydrolyzed with aqueous NaOH to give the 4-carboxy derivative (86INIP157279). Heating pyrimido[6,1-a]isoquinolin-4-one(132) in methanol gave the tetracyclic compound 133 (86CB2553). The reaction of 1-amino-2-[(2,3,4trimethylphenyl)amino]-6,7-dihydro-4H-pyrimido[6,1-a] isoquinolin-4-one hydrochloride (134) with HN02or with triethyl orthoesters gave the tetracyclic compounds 135 and 136, respectively [89H(29)1929].

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


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