Studies on the reaction of N-(3-carbethoxy-4,5,6,7-tetrahydrobenzo[b]thien-2-yl)-N′-phenylthiourea with hydrazine hydrate (Part 1)
The reaction of N‐(3‐carbethoxy‐4,5,6,7‐tetrahydrobenzo[b]thien‐2‐yl)‐N′‐phenylthiourea (1) with hydrazine hydrate in 1‐butanol afforded a mixture of compounds 2, 3 and 4. Treatment of 3 and 4 with nitrous acid gave 6 and 8 respectively, while reactions of 3 with acetylacetone gave 7. Synthesis of t...
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| Published in: | Journal of heterocyclic chemistry Vol. 45; no. 2; pp. 467 - 473 |
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| Abstract | The reaction of N‐(3‐carbethoxy‐4,5,6,7‐tetrahydrobenzo[b]thien‐2‐yl)‐N′‐phenylthiourea (1) with hydrazine hydrate in 1‐butanol afforded a mixture of compounds 2, 3 and 4. Treatment of 3 and 4 with nitrous acid gave 6 and 8 respectively, while reactions of 3 with acetylacetone gave 7. Synthesis of tetracyclic compounds 9a‐f and 11 from the reactions of 3 with ethyl orthoformate or appropriate acids, acid chloride, carbon disulphide and/or ethyl chloroformate. Also its reaction with isothiocyanate derivatives gave the corresponding thiosemicarbzides 12a,b which on, refluxing in alcoholic KOH gave the unexpected tetracyclic products 14a,b. Similarly the tetracyclic compounds 16a‐e and 19 were obtained by cyclization of 4 and 18 respectively. |
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| AbstractList | magnified image
The reaction of
N
‐(3‐carbethoxy‐4,5,6,7‐tetrahydrobenzo[
b
]thien‐2‐yl)‐
N
′‐phenylthiourea (
1
) with hydrazine hydrate in 1‐butanol afforded a mixture of compounds
2, 3
and
4
. Treatment of
3
and
4
with nitrous acid gave
6
and
8
respectively, while reactions of
3
with acetylacetone gave
7
. Synthesis of tetracyclic compounds
9a‐f
and
11
from the reactions of
3
with ethyl orthoformate or appropriate acids, acid chloride, carbon disulphide and/or ethyl chloroformate. Also its reaction with isothiocyanate derivatives gave the corresponding thiosemicarbzides
12a,b
which on, refluxing in alcoholic KOH gave the unexpected tetracyclic products
14a,b
. Similarly the tetracyclic compounds
16a‐e
and
19
were obtained by cyclization of
4
and
18
respectively. The reaction of N‐(3‐carbethoxy‐4,5,6,7‐tetrahydrobenzo[b]thien‐2‐yl)‐N′‐phenylthiourea (1) with hydrazine hydrate in 1‐butanol afforded a mixture of compounds 2, 3 and 4. Treatment of 3 and 4 with nitrous acid gave 6 and 8 respectively, while reactions of 3 with acetylacetone gave 7. Synthesis of tetracyclic compounds 9a‐f and 11 from the reactions of 3 with ethyl orthoformate or appropriate acids, acid chloride, carbon disulphide and/or ethyl chloroformate. Also its reaction with isothiocyanate derivatives gave the corresponding thiosemicarbzides 12a,b which on, refluxing in alcoholic KOH gave the unexpected tetracyclic products 14a,b. Similarly the tetracyclic compounds 16a‐e and 19 were obtained by cyclization of 4 and 18 respectively. |
| Author | El-Sawaisi, Suliman M. El-Naggar, Galal M. El-Sherief, Hassan A. H. Hozien, Zeinab A. |
| Author_xml | – sequence: 1 givenname: Hassan A. H. surname: El-Sherief fullname: El-Sherief, Hassan A. H. organization: Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt – sequence: 2 givenname: Galal M. surname: El-Naggar fullname: El-Naggar, Galal M. organization: Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt – sequence: 3 givenname: Zeinab A. surname: Hozien fullname: Hozien, Zeinab A. organization: Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt – sequence: 4 givenname: Suliman M. surname: El-Sawaisi fullname: El-Sawaisi, Suliman M. organization: Chemistry Department, Faculty of Science, 7th October University, Misurata, Libya |
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| CitedBy_id | crossref_primary_10_1016_j_bmcl_2017_05_030 crossref_primary_10_5155_eurjchem_2_2_251_259_380 crossref_primary_10_1002_chin_200830157 crossref_primary_10_1080_00397911_2021_1936058 crossref_primary_10_1007_s12039_017_1223_4 |
| Cites_doi | 10.1002/jhet.5570180111 10.3987/R-1987-05-1303 10.1016/S0040-4020(97)00847-8 10.1016/0223-5234(88)90142-0 10.1002/jhet.5570210241 10.1016/0223-5234(96)88255-9 10.1016/0223-5234(91)90065-U 10.1002/zfch.19690090702 10.1246/bcsj.56.1227 10.1080/10426509108036785 10.1246/bcsj.57.1138 10.1002/jhet.5570180109 10.1007/BF00906224 10.1002/jps.2600650507 10.1016/0223-5234(93)90112-R 10.1002/ardp.19923250510 10.1055/s-2005-865289 10.1248/yakushi1947.109.7_464 10.1002/jhet.5570250349 10.3390/50600835 |
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| Title | Studies on the reaction of N-(3-carbethoxy-4,5,6,7-tetrahydrobenzo[b]thien-2-yl)-N′-phenylthiourea with hydrazine hydrate (Part 1) |
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