Synthesis and Central Nervous System Stimulant Activity of 5,8-Methanoquinazolines Fused with Imidazole, Thiadiazole, Pyrimidine, and1,3,5-Triazine. -The synthesis of a variety of new camphor-pyrimidines fused with azoles [cf. (VII), (XV), (XVI)], pyrimidines [cf. (IX), (XIII)], and triazine (XI) f
Synthesis and central nervous system stimulant activity of 5,8-methanoquinazolines fused with imidazole, thiadiazole, pyrimidine and 1,3,5-triazine
✍ Scribed by Sbin-Ichi Nagai; Taisei Ueda; Akito Nagatsu; Keiko Nakaoka; Nobutoshi Murakami; Jinsaku Sakakibara; Michiko Fujita; Yoshihiro Hotta
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1998
- Tongue
- English
- Weight
- 287 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
5,8‐Methanoquinazolines fused with imidazoles 4a‐4b, thiadiazoles 5–6, pyrimidines 7, 9, 11 and 12, and 1,3,5‐triazine 13 were prepared starting from (5__R__,8__S__)‐2‐amino‐8,9,9‐trimethyl‐5,6,7,8‐tetrahydro‐5,8‐methanoquinazoline 3. Most compounds possessed central nervous system stimulant activities.
📜 SIMILAR VOLUMES
## Abstract Starting from 3‐chloro‐5,8‐methanoquinazoline **1** and 3‐chloro‐bornano[1,2,4]triazine **7**, the novel 5,8‐methanoquinazolines **5a‐b** and bornano[1,2,4]triazines **10a‐b** fused with imidazole and pyrimidine were prepared. None of these compounds showed any satisfactory central nerv
## Abstract 5,8‐Methanoquinazolines fused with 1,2,4‐triazole 4–5, tetrazole 6, and 1,2,4‐triazine 8 were prepared starting from 2‐hydrazino‐5,8‐methanoquinazoline 3. Compound 3 and 6 showed the most potent central nervous system (CNS) stimulant activities.
## Abstract Reactions of camphor‐1,2,3‐triazine 1 with diphenylcyclopropenone 2 gave two cycloadducts; 6,9‐methanopyrazolo[1,2‐__b__][1,2,3]benzotriazinones 3–4. Oxidation of 1 with 3‐chloroperbenzoic acid gave 1‐oxide 5 as the major compound along with a trace of 1,2‐dioxide 6.