Facile Synthesis of 6-Aryl-1,3-dimethyl-5H-pyrimido[4,5-b][1,4]diazepine-2,4(1H,3H)-diones

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Title:Facile Synthesis of 6-Aryl-1,3-dimethyl-5H-pyrimido[4,5-b][1,4]diazepine-2,4(1H,3H)-diones
Creators:
Taghavi-Moghadam, Shahriyar
Stumpf, Rüdiger
Fischer, Helmut
Pfleiderer, Wolfgang
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 2, pp. 313-320
Uncontrolled Keywords:Purines, Orthoester condensation, Pteridines, Pyrimidines, Crystal structure, Pyrimido[4,5-<i>b</i>][1,4]diazepines

Abstract

A facile procedure for the preparation of 6-aryl-1,3-dimethyl-5<i>H</i>-pyrimido[4,5-<i>b</i>][1,4]diazepine2,4(1<i>H</i>,3<i>H</i>)-diones <strong>8</strong>, <strong>9</strong> from 6-amino-5-arylideneamino-1,3-dimethyluracils <strong>1</strong>, <strong>2</strong> and triethyl orthoacetate (<strong>3</strong>) in a two-step reaction <i>via</i> 6-aryl-8-ethoxy-6,7-dihydro-1,3-dimethyl-5<i>H</i>-pyrimido[4,5-<i>b</i>][1,4]diazepine-2,4(1<i>H</i>,3<i>H</i>)-diones <strong>6</strong>, <strong>7</strong> is described. Condensation of <strong>1</strong> with diethoxymethyl acetate (<strong>10</strong>) resulted in the formation of (1,3-dimethyl-2,6-(1<i>H</i>,3<i>H</i>)-dioxopurin-7-yl)(phenyl)methyl acetate (<strong>11</strong>) and a small amount of 1,3-dimethyl-6-phenylpyrazino[2,3-<i>d</i>]pyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione (<strong>12</strong>). The structures of <strong>6</strong> and <strong>11</strong> were unambiguously confirmed by single-crystal X-ray diffraction analysis. <p>

Title:Facile Synthesis of 6-Aryl-1,3-dimethyl-5H-pyrimido[4,5-b][1,4]diazepine-2,4(1H,3H)-diones
Creators:
Taghavi-Moghadam, Shahriyar
Stumpf, Rüdiger
Fischer, Helmut
Pfleiderer, Wolfgang
Uncontrolled Keywords:Purines, Orthoester condensation, Pteridines, Pyrimidines, Crystal structure, Pyrimido[4,5-<i>b</i>][1,4]diazepines
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:2
Page Range:pp. 313-320
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990313UNSPECIFIED
ID Code:1478
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:10

Citation

Taghavi-Moghadam, Shahriyar; Stumpf, Rüdiger; Fischer, Helmut; Pfleiderer, Wolfgang (1999) Facile Synthesis of 6-Aryl-1,3-dimethyl-5H-pyrimido[4,5-b][1,4]diazepine-2,4(1H,3H)-diones. Collection of Czechoslovak Chemical Communications, 64 (2). pp. 313-320. ISSN 0010-0765

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