Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: applications towards the synthesis of drugs

Kumar Dinesh; Jadhavar Pradeep S.; Nautiyal Manesh; Sharma Himanshu; Meena Prahlad K.; Adane Legesse; Pancholia Sahaj; Chakraborti Asit K.

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Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: applications towards the synthesis of drugs

机译：方便合成2,3-二取代的喹唑啉-4（3H） - 酮和2- styryl-3-取代的喹唑啉-4（3H） - 酮：对药物合成的应用

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Simple, convenient, and green synthetic protocols have been developed for the one pot synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones under catalyst and solvent free conditions. The multicomponent reaction (3-MCR) involving isatoic anhydride, an amine, and orthoester afforded the 2,3-disubstituted quinazolin-4(3H)-ones in excellent yields under classical heating at 120 degrees C for 5 h or under microwave irradiation at 140 degrees C for 20-30 min. The use of ammonium acetate instead of the amine provides the 2-substituted quinazolin-4(3H)-ones. The reactions are compatible with various substituted isatoic anhydrides, aryl/heteroaryl/alkyl/cycloalkyl amines, and orthoesters. The strategies are extended to the one pot tandem condensation involving isatoic anhydride, an amine, orthoester, and aldehyde to afford highly functionalized (E)-3-aryl/heteroaryl-2-styrylquinazolin/(2-(heteroaryl) vinyl) quinazolin-4(3H)-ones. The applications of the methodologies are demonstrated through the synthesis of various drugs which act on the central nervous system such as methaqualone, mebroqualone, mecloqualone, piriquialone, and diproqualone.

机译：已经为催化剂和溶剂下的2,3-二取代的喹唑啉-4（3H）和2- Styryl-3-取代的喹唑啉-4（3H）酮开发了简单，方便和绿色的合成方案。在催化剂和溶剂下自由条件。涉及异羟酸酐，胺和正原蛋白酶的多组分反应（3-MCR），得到2,3-二取代的喹唑啉-4（3H） - 在经典加热下在120℃下的优异产率为5小时或在微波辐射下140℃持续20-30分钟。乙酸铵代替胺的使用提供了2-取代的喹唑啉-4（3H）酮。反应与各种取代的异酸酐，芳基/杂芳基/烷基/环烷基胺和矫酯剂相容。该策略延伸到涉及异烟酐，胺，正螺母和醛的一个罐串联冷凝，得到高官能化（E）-3-芳基/杂芳基-2-苯基喹唑啉/（2-（杂芳基）乙烯基）喹唑啉-4 （3h） - -。通过对中枢神经系统的合成来证明方法的应用是通过对甲基醌，Mebrogalone，MeCloqualone，吡喹酮和二维萘醛酮等作用的各种药物来证明。

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《RSC Advances》 |2015年第39期|共7页
作者
Kumar Dinesh; Jadhavar Pradeep S.; Nautiyal Manesh; Sharma Himanshu; Meena Prahlad K.; Adane Legesse; Pancholia Sahaj; Chakraborti Asit K.;
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Natl Inst Pharmaceut Educ &

Res Dept Med Chem Sas Nagar 160062 Punjab India;

Natl Inst Pharmaceut Educ &

Res Dept Med Chem Sas Nagar 160062 Punjab India;

Natl Inst Pharmaceut Educ &

Res Dept Med Chem Sas Nagar 160062 Punjab India;

Natl Inst Pharmaceut Educ &

Res Dept Med Chem Sas Nagar 160062 Punjab India;

Natl Inst Pharmaceut Educ &

Res Dept Med Chem Sas Nagar 160062 Punjab India;

Natl Inst Pharmaceut Educ &

Res Dept Med Chem Sas Nagar 160062 Punjab India;

Natl Inst Pharmaceut Educ &

Res Dept Med Chem Sas Nagar 160062 Punjab India;

Natl Inst Pharmaceut Educ &

Res Dept Med Chem Sas Nagar 160062 Punjab India;

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中图分类化学;
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1. Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: applications towards the synthesis of drugs [J] . Kumar Dinesh, Jadhavar Pradeep S., Nautiyal Manesh, RSC Advances . 2015,第39期

机译：方便合成2,3-二取代的喹唑啉-4（3H） - 酮和2- styryl-3-取代的喹唑啉-4（3H） - 酮：对药物合成的应用
2. Convenient one-pot synthesis of N~3-substituted pyrido[2,3-d]-, pyrido[3,4-dl-, pyrido[4,3-d]-pyrimidin-4(3H)-ones, and quinazolin-4(3H)-ones analogs [J] . Emmanuel Deau, Damien Hedou, Elizabeth Chosson Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2013,第27期

机译：方便的一锅法合成N〜3-取代的吡啶并[2,3-d]-，吡啶并[3,4-dl-，吡啶并[4,3-d]-嘧啶-4（3H）-和喹唑啉-4（3H）-ones类似物
3. Synthesis And Anagesic activities of Quinazolin-4(3H)-One, 2-Methyl-4(3H)-Quinazolinone and 2–Phenyl-4(3H)-quinazolin-4(3H)–one [J] . P.O. Osarumwense, M.O. Edema, C.O. Usifoh Journal of Drug Delivery and Therapeutics . 2020,第4as期

机译：喹唑啉-4（3H） - ONE，2-甲基-4（3H） - 喹唑啉酮和2-苯基-4（3H）-Quinazolin-4（3H） - One的合成和肾上腺素活性
4. Synthesis and Characterization of New 2-Methoxy-Thieno2,3-dpyrimidin-4(3H)-One [C] . Lian-Ying Lu, Zhong-Shan Yu, Zheng-Dong Fang, CEAM 2012 . 2012

机译：新型2-甲氧基 - 噻吩的合成与表征2,3-D嘧啶-4（3H） - 酮
5. Resolution of the diastereomers of N-1',N-3'-disubstituted, 2'H,3H,5'H-spiro[2-benzofuran-1,4'-imidazolidine]-2'3,5'-trione and their anticonvulsant activities [D] . Sadarangani, Ishwar R. 2012

机译：N-1'，N-3'-双取代，2'H，3H，5'H-螺[2-苯并呋喃-1,4'-咪唑烷] -2'3,5'-三酮和他们的抗惊厥活动
6. Design synthesis antiviral bioactivities and interaction mechanisms of penta-14-diene-3-one oxime ether derivatives containing a quinazolin-4(3H)-one scaffold [O] . Lijuan Chen, Xiaobin Wang, Xu Tang, 2019

机译：包含喹唑啉-4（3H）-一个骨架的五-14-二烯-3-酮肟醚衍生物的设计合成抗病毒生物活性和相互作用机理
7. Amberlite IR-120 H+ Resin, an Efficient and Recyclable Solid Phase Catalyst for the Synthesis of 2, 3-Disubstituted Quinazolin-4(3H)-Ones: A Greener Approach [O] . Ravi Kumar G. M. V. N. A. R, Thangamani Arumugam, Venkata Reddy Gayam, 2017

机译：琥珀酸酯IR-120h +树脂，用于合成2,3-二取代的喹唑啉-4（3H） - 导致的高效和可回收的固相催化剂：更绿色的方法

Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: applications towards the synthesis of drugs

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