Synthesis of furano[2,3-c] /pyrrolo[2,3-c]coumarins and synthesis of 1(H)-[1]benzopyrano[3,4-b][1]benzopyrano[3’,4’-d] furan-7(H)-ones /1(H)-[1]benzopyrano[3,4-b][1]benzopyrano [3’,4’-d]pyrrole-7(H)-ones

  • Mahesh K. Pandya
  • Mehulsinh R. Chhasatia
  • Nileshkumar D. Vala
  • Tapan H. Parekh

Abstract

A series of synthesis of various 1-aryl-furano[2,3-c] and 1-phenyl-2-methyl-furano [2,3-c]coumarins;1-aryl-pyrrolo[2,3-c]and1-phenyl-2methylpyrrolo[2,3c]coumarins; 1aryl1H1] benzopyrano[3,4,-b][1]benzpyrano [3’,4’-d]furan-7H-ones and 1-aryl-1(H)-[1]benzopyrano[3,4,-b][1]benzpyrano[3’,4’-d]pyrrole-7(H)-ones. 1-Aryl-furano [2,3-c]coumarins and 1-phenyl-2-methyl-furano[2,3-c]coumarin have been synthesized by reacting 3-hydroxy coumarin with various 2-aryl-1-nitro-ethenes and 1-phenyl-2-nitro-propene respectively in the presence of piperidine and methanol as solvent. 1-Aryl-pyrrolo [2,3-c]coumarins and 1-phenyl-2-methyl-pyrrolo[2,3-c] coumarin also have been synthesised by reacting 3-amino coumarin with  various 2-aryl-1-nitro-ethenes and 1-phenyl-2-nitro-propene respectively in the presence of piperidine and methanol. The formation of furan and pyrrole nucleus in all above compounds follows Nef reaction mechanism. Using the Nef reaction, synthesis of various 1-aryl-1(H)-[1]benzopyrano[3,4,-b][1]benzpyrano[3’,4’-d]furan-7(H)-ones have been carried out  by reacting various 4-hydroxy coumarins with various 3-nitro-2-aryl-2H-[1]benzopyrans in the presence of piperidine and methanol. Similarly synthesis of various 1-aryl-1(H)-[1]benzopyrano[3,4,-b][1]benzpyrano [3’,4’-d]pyrrole-7(H)-ones also have been carried out by reacting various 4-hydroxy coumarins with various 3-nitro-2-aryl-2H-[1]benzopyrans in the presence of ammoniun acetate  and acetic acid.


Keywords: Furan, Pyrrolo,Coumarin, Benzopyrano.

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Author Biographies

Mahesh K. Pandya

Department of Chemistry Sardar Patel University,Vallabh Vidyanagar, Gujarat, (INDIA).

Mehulsinh R. Chhasatia

Department of Chemistry Sardar Patel University,Vallabh Vidyanagar, Gujarat, (INDIA).

Nileshkumar D. Vala

Department of Chemistry Sardar Patel University,Vallabh Vidyanagar, Gujarat, (INDIA).

Tapan H. Parekh

Department of Chemistry Sardar Patel University,Vallabh Vidyanagar, Gujarat, (INDIA).

References

1. (i) S. Shivkumar and S. Bhaduri ,Indian journal of chemistry, 22B, 725, (1983). (ii)S. P. Herimath , A. S. Jivanagi and M. G. Purohit,Indian journal of chemistry, 32B, 662, (1993).
2. E. Spath and F. KuffnerMonatsch, 69, 75 (1936).
3. A. B. LernerJ. Invest. Dermatol., 20, 299 (1953).
4. M. A. Pathak and J. H. FellmanNature, 185, 382 (1960).
5. C. N. Patel PhD Thesis, “synthetic studies in coumarin and coumarin based polymers”, Sardar Patel University, V.V.Nagar (2001).
6. A. K. Mitra and J. Mitra,Indian journal of chemistry, 33(B), 276-79, (1994).
7. K. N. Trivedi and R. R. Shah, Indian journal of chemistry, 210-12, (1981).
8. V. K. Ahluwalia, M. C. Gupta and S. Mehta, Indian journal of chemistry, 17(B), 332-335, (1979).
9. C. Majumdar, and R. De, J.chem.Soc.Perkin Trans.1, 1901-1905, (1989).
10. M. Maheshwari, V. K. Mahesh, R. Sharma,Indian journal of chemistry, 23(B), 486-88, (1984).
11. K. N. Trivedi and Y. A. Shikh,J.Indian Chem.Soc.,Vol.L, 41-44, (1973).
12. Khan, Misbahul ain, Morely, M. L. Brito,Journal of Heterocyclic Chemistry, 15(8), 1399-401, (1978).
13. V. P. PandyaPhD Thesis, “Synthetic studies in heterocyclic substituted and fused coumarins and coumarin based polyethers”, Sardar Patel University, V.V.Nagar (2004).
14. J. M. Pepper and M. Shaha Can. J. Chem., 42, 113, (1964).
15. A. P. Bhaduri and P. K. Arora Indian journal of chemistry, 20(B), 951-54, (1981).
16. (i) F. M. Dean, A. Robertson and W. B. Whalley J. Chem. Soc., 895, (1950).
(ii) K. N. Trivedi and S. Sethna J. Org. Chem., 25, 1817, (1960).
17. F. W. Linch J. Chem. Soc., 101, 1912, (1962).
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Pandya MK, Chhasatia MR, Vala ND, Parekh TH. Synthesis of furano[2,3-c] /pyrrolo[2,3-c]coumarins and synthesis of 1(H)-[1]benzopyrano[3,4-b][1]benzopyrano[3’,4’-d] furan-7(H)-ones /1(H)-[1]benzopyrano[3,4-b][1]benzopyrano [3’,4’-d]pyrrole-7(H)-ones. JDDT [Internet]. 15Aug.2019 [cited 18Jun.2021];9(4-s):32-. Available from: https://jddtonline.info/index.php/jddt/article/view/3243