Roma G, Balbi A, Ermili A, Vigevani E
Farmaco Sci. 1983 Aug;38(8):546-58.
The reaction of 4-(dialkylamino)-1,3-dihydro-2H-1,5-benzodiazepin-2-ones (I a-c) with N,N-dimethylformamide in the presence of phosphorus pentachloride at room temperature gave rise to the formation of 4-(dialkylamino)-3-[(dimethylamino)methylene]-1,3-dihydro-2H-1,5-benzodiazepin- 2-ones (IX a-c) which were useful starting materials to achieve the synthesis of tricyclic 1,5-benzodiazepine derivatives. Actually (IX a), selected for the smallest steric hindrance of the 4-dialkylamino substituent, by reaction with hydrazines afforded pyrazolo[3,4-b][1,5]benzodiazepine derivatives whereas reaction with guanidine or amidines gave 5H-pyrimido-[4,5-b][1,5]benzodiazepine derivatives. The structure of isomeric N-methyl-pyrazoles (X c) and (XI a) and of N-phenylpyrazole (X b) were elucidated by comparison with compounds prepared by unequivocal chemical methods. Pharmacological evaluation of some of the products showed only generic CNS depressant activity.
4-（二烷基氨基）-1,3-二氢-2H-1,5-苯并二氮杂䓬-2-酮（I a - c）在室温下于五氯化磷存在下与N，N-二甲基甲酰胺反应，生成了4-（二烷基氨基）-3- [（二甲基氨基）亚甲基]-1,3-二氢-2H-1,5-苯并二氮杂䓬-2-酮（IX a - c），它们是合成三环1,5-苯并二氮杂䓬衍生物的有用起始原料。实际上，（IX a）因4-二烷基氨基取代基的空间位阻最小而被选用，它与肼反应生成吡唑并[3,4 - b][1,5]苯并二氮杂䓬衍生物，而与胍或脒反应则生成5H-嘧啶并[4,5 - b][1,5]苯并二氮杂䓬衍生物。通过与用明确化学方法制备的化合物进行比较，阐明了异构体N-甲基吡唑（X c）和（XI a）以及N-苯基吡唑（X b）的结构。对其中一些产物的药理评价表明仅具有一般的中枢神经系统抑制活性。
