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Saturated heterocycles. 254. synthesis and stereochemistry of saturated or partially saturated pyridazino-[6,1-b]- and phthalazino[1,2-b]quinazolinones

✍ Scribed by GÁBor Bernáth; Ferenc Miklós; GÉZa Stájer; PÁL Sohár; Zsolt Böcskei; DÓRa Menyhárd

Publisher
Journal of Heterocyclic Chemistry
Year
1998
Tongue
English
Weight
553 KB
Volume
35
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

By the reaction of anthranilic hydrazide 1 with cis‐2‐(p‐methylbenzoyl)‐1‐cyclohexanecarboxylic acid 2a or diendo‐3‐(p‐methylbenzoyl)bicyclo[2.2.1]heptane‐2‐carboxylic acid 2b, fused tetra‐ and pentacyclic ring systems 3a, b were prepared, trans‐2‐Amino‐1‐cyclohexanecar‐bohydrazide 4b was reacted with 3‐(p‐chlorobenzoyl)propionic acid 5 to yield the pyridazino[6,1‐b]quinazolinone 6. From the reaction of cis‐2‐amino‐1‐cyclohexanecarbohydrazide 4a with 2a, three isomeric partially saturated 8__H__‐phthalazino[1,2‐b]quinazolin‐8‐ones 7a‐c were formed. The reaction of diexo‐2‐aminobicyclo[2.2.1]heptane‐3‐carbohydrazide 4c and 2a furnished the pentacyclic derivatives 8 and 9 containing a 3‐aryl‐4,5‐dihydropyridazine or 3‐arylhexahydropyridazine ring C with cis annelated C/D rings. The formation of 8 and 9 involving different ring systems can be rationalized by two reaction pathways: (i) in the bislactam 9 the carboxyl group acylates the hydrazide, while (ii) in 8 it forms a pyridazine ring with the cyclic amino group by cyclocondensation. The structures of the products were elucidated by ^1^H and ^13^C nmr methods, including DEPT, DNOE and 2D‐HSC measurements.

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