Quinazolines. VII. Synthesis of 1,3‐Diamino‐5,6‐dihydrobenzo[f]quinazolines
- 1 April 1972
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 9 (2) , 263-273
- https://doi.org/10.1002/jhet.5570090214
Abstract
Eighteen new 1,3‐diamino‐5,6‐dihydrobenzo[f] quinazolines (6, R. = alkyl, Cl, MeO) were synthesized via the condensation of appropriate 2‐tetralones with cyanoguanidine under fusion conditions. Methods were developed for the preparation of a number of heretofore undescribed 2‐tetralones as precursors. The final products can be viewed as conformationally rigid analogs of pyrimethamine (2), and are of interest as inhibitors of dihydrofolate reductase and as potential antimalarial and antitumor agents.Keywords
This publication has 30 references indexed in Scilit:
- Quinazolines. VI. Synthesis of 2,4-diaminoquinazolines from anthranilonitrilesJournal of Medicinal Chemistry, 1970
- [1] Benzopyrano[3,4‐d] pyrimidines and [1] benzothiopyrano[3,4‐d] pyrimidines. Two new heterocyclic ring systemsJournal of Heterocyclic Chemistry, 1970
- Synthesis of 2,4‐diamino‐9H‐indeno[2,1‐d]pyrimidinesJournal of Heterocyclic Chemistry, 1969
- Synthesis of new chlorine-substituted derivatives of 2-tetraloneThe Journal of Organic Chemistry, 1968
- The Stereochemistry of Doubly Bridged Biphenyls: Synthesis, Spectral Properties, and Optical StabilityJournal of the American Chemical Society, 1964
- A Stereospecific Route to the Dehydroabietic Acid Configuration1Journal of the American Chemical Society, 1961
- Peresters. IV. Substituent Effects upon the Concerted Decomposition of t-Butyl Phenylperacetates1Journal of the American Chemical Society, 1960
- The effects of substitution on the ultra-violet absorption spectra of phenylpyrimidinesJournal of the Chemical Society, 1954
- 234. The synthesis of hydrocarbons of high molecular weight. Part II. Some di- and tri-n-alkylnaphthalenesJournal of the Chemical Society, 1951
- 424. Butylnaphthalenes and their derivatives. Part II. Derivatives of 2-tert.-butylnaphthalene, and the orientation of two di-tert.-butylnaphthalenesJournal of the Chemical Society, 1949