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

G. Bernáth, F. Miklos, G. Stájer, P. Sohár, Z. Bocskei, D. Menyhard

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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- cyclohexanecarbohydrazide 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 8H-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 pentacylcic derivatives 8 and 9 containing a 3-aryl-4,5- dihydropyridazine or 3-aryl-hexahydropyridazine ring 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 1H and 13c nmr method, including DEPT, DNOE and 2D-HSC measurements.

Original languageEnglish
Pages (from-to)201-208
Number of pages8
JournalJournal of Heterocyclic Chemistry
Volume35
Issue number1
Publication statusPublished - 1998

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Quinazolinones
Heptanes
Stereochemistry
Carboxylic Acids
Derivatives
cyclohexanecarboxylic acid
propionic acid
pyridazine
carbohydrazide
bicyclo(2.2.1)heptene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Saturated heterocycles. 254 [1]. Synthesis and stereo-chemistry of saturated or partially saturated pyridazino-[6,1-b]-and phthalazino[1,2- b]quinazolinones",
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- cyclohexanecarbohydrazide 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 8H-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 pentacylcic derivatives 8 and 9 containing a 3-aryl-4,5- dihydropyridazine or 3-aryl-hexahydropyridazine ring 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 1H and 13c nmr method, including DEPT, DNOE and 2D-HSC measurements.",
author = "G. Bern{\'a}th and F. Miklos and G. St{\'a}jer and P. Soh{\'a}r and Z. Bocskei and D. Menyhard",
year = "1998",
language = "English",
volume = "35",
pages = "201--208",
journal = "Journal of Heterocyclic Chemistry",
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TY - JOUR

T1 - Saturated heterocycles. 254 [1]. Synthesis and stereo-chemistry of saturated or partially saturated pyridazino-[6,1-b]-and phthalazino[1,2- b]quinazolinones

AU - Bernáth, G.

AU - Miklos, F.

AU - Stájer, G.

AU - Sohár, P.

AU - Bocskei, Z.

AU - Menyhard, D.

PY - 1998

Y1 - 1998

N2 - 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- cyclohexanecarbohydrazide 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 8H-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 pentacylcic derivatives 8 and 9 containing a 3-aryl-4,5- dihydropyridazine or 3-aryl-hexahydropyridazine ring 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 1H and 13c nmr method, including DEPT, DNOE and 2D-HSC measurements.

AB - 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- cyclohexanecarbohydrazide 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 8H-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 pentacylcic derivatives 8 and 9 containing a 3-aryl-4,5- dihydropyridazine or 3-aryl-hexahydropyridazine ring 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 1H and 13c nmr method, including DEPT, DNOE and 2D-HSC measurements.

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