Resolving the Mystery of Ring Opening in the Synthesis of Benzo[d][1, 3]oxazin-4-one and Quinazolin-4(3H)-one

Author(s): Harun Patel*, Rahul Pawara, Sanjay Surana.

Journal Name: Letters in Organic Chemistry

Volume 16 , Issue 11 , 2019

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Abstract:

Quinazoline is the six-membered heterocyclic ring system reported for its versatile biological activities. This characteristic feature of quinazoline makes it a good template for a lead generation library. Ring opening is one of the major concerns in the synthesis of quinazolin-4(3H)-one that results in diamide formation. Here, alternative fusion strategy is reported, which is a time-saving and costeffective method to overcome the ring opening problem associated with the synthesis of benzo[ d][1,3]oxazin-4-one and quinazolin-4(3H)-one.

Keywords: Quinazoline, ring opening, fusion, six-membered heterocyclic ring, fusion strategy, diamide formation.

[1]
Rohini, R.; Shanker, K.; Reddy, P.M.; Ho, Y.; Ravinder, P.V. Eur. J. Med. Chem., 2009, 44, 3330.
[2]
Pandey, S.K.; Singh, A.; Singh, A. Nizammudin. Eur. J. Med. Chem., 2009, 44, 1188.
[3]
Mohamed, M.S.M.; Kamel, M.E.; Kassem, M.M.; Abotaleb, N.; Abd El-Moez, S.I.; Ahmed, M.F. Eur. J. Med. Chem., 2010, 45, 3311.
[4]
Abdel-Wahab, B.F.; Abdel-Aziz, H.A.; Ahmed, E.M. Monatsh. Chem., 2009, 140, 601.
[5]
Kadi, A.A.; Al-Abdullah, E.S.; Shehata, I.A.; Habib, E.A.; Ibrahim, T.M. Eur. J. Med. Chem., 2010, 45, 5006.
[6]
Geitmann, M.; Unge, T.; Danielson, U.H. J. Med. Chem., 2006, 49, 2375.
[7]
Srivastava, A.; Kumar, A. Eur. J. Med. Chem., 2002, 37, 873.
[8]
Varsha, J.; Pradeep, M.; Sushil, K.; Stables, J.P. Eur. J. Med. Chem., 2008, 43, 135.
[9]
Patel, H.M.; Surana, S.; Shirkhedkar, A.; Kulkarni, A.; Pardeshi, C. RSC Adv, 2016, 6, 44435.
[10]
Kurogi, Y.; Inoue, Y.; Tsutsumi, K.; Nakamura, S.; Nagao, K.; Yoshitsugu, H.; Tsuda, Y. J. Med. Chem., 1996, 39, 1433.
[11]
Al-Obaid, A.M.; Abdel-Hamide, S.G.; El-Kashef, H.A.; Abdel-Aziz, A.A.M.; El-Azab, A.S.; Al-Khamees, H.A.; El-Subbagh, H.I. Eur. J. Med. Chem., 2009, 44, 2379.
[12]
Alam, M.J.; Alam, O.; Naim, M.J.; Alam, P.A. Scaffold. Int. J. Adv. Res., 2015, 3, 1656.
[13]
McLaughlin, N.P.; Evans, P. J. Org. Chem., 2010, 75, 518.
[14]
Kobayashi, S.; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, H.S.; Wataya, Y. J. Org. Chem., 1999, 64, 6833.
[15]
Keller, T.L.; Zocco, D.; Sundrud, M.S.; Hendrick, M.; Edenius, M.; Yum, J.; Kim, Y.J.; Lee, H.K.; Cortese, J.F.; Wirth, D.F.; Dignam, J.D.; Rao, A.; Yeo, C.Y.; Mazitschek, R.; Whitman, M. Nat. Chem. Biol., 2012, 8, 311.
[16]
Ochiai, T.; Ishida, R. Jpn. J. Pharmacol., 1982, 32, 427.
[17]
Pasqualotto, A.C. Thiele; K.O.; Goldani, L.Z. Curr. Opin. Investig. Drugs, 2010, 11, 165.
[18]
Al-Obaid, A.M.; Abdel-Hamide, S.G.; El-Kashef, H.A.; Abdel-Aziz, A.A.M.; El-Azab, H.; Al-Khamees, A.; El-Subbagh, H.I. Eur. J. Med. Chem., 2009, 44, 2379.
[19]
Al-Omary, F.A.M.; Abouzeid, L.A.; Nagi, M.N.; Habib, E.E.; Abdel-Aziz, A.A.M.; El-Azab, A.S.; Abdel-Hamide, S.G.; Al-Omar, M.A.; Al-Obaid, A.M.; El-Subbagh, H.I. Bioorg. Med. Chem., 2010, 18, 2849.
[20]
Al-Rashood, S.T.; Aboldahab, I.A.; Nagi, M.N.; Abouzeid, L.A.; Abdel-Aziz, A.A.M.; Abdel-Hamide, S.G.; Youssef, K.M.; Al-Obaid, A.M.; El-Subbagh, H.I. Bioorg. Med. Chem., 2006, 14, 8608.
[21]
Aamer, S.; Mauricio, F.E.; Michael, B. J. Org. Chem., 2012, 77, 4688-4695.


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Article Details

VOLUME: 16
ISSUE: 11
Year: 2019
Page: [898 - 905]
Pages: 8
DOI: 10.2174/1570178616666181217114030
Price: $58

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