Multistep Flow Synthesis of 5-Amino-2-aryl-2H-[1,2,3]-triazole-4- carbonitrilesultistep Flow Synthesis of 5-Amino-2-aryl-2H-[1,2,3]-triazole-4- carbonitriles

Using the Uniqsis FlowSyn flow chemistry system researchers from the UCB Biopharma. Belgium have developed a flow synthesis of 2-substituted 1,2,3-triazoles that demonstrates improvements over the conventional batch route.
The route involves the diazotisation of anilines and condensation with malononitrile followed by the nucleophilic addition of ammonia or an alkylamine and finally a novel copper catalysed cyclisation. The intermediate azide was generated and consumed in situ which enabled safe scale up under the flow-through conditions employed.

J. Jacq, P. Pasau, Chem Eur. J., 2014, 20, (38), 12223.

DOI: 10.1002/chem.201402074

Multistep Flow Synthesis of 5-Amino-2-aryl-2H-[1,2,3]-triazole-4-carbonitriles

Authors, Dr. Jérôme Jacq, Dr. Patrick Pasau

Corresponding author

• E-mail address: patrick.pasau@ucb.com

1. UCB Biopharma, Avenue de l'Industrie, 1420 Braine l'Alleud (Belgium)

• UCB Biopharma, Avenue de l'Industrie, 1420 Braine l'Alleud (Belgium)===

1,2,3-Triazole has become one of the most important heterocycles in contemporary medicinal chemistry. The development of the copper-catalyzed Huisgen cycloaddition has allowed the efficient synthesis of 1-substituted 1,2,3-triazoles. However, only a few methods are available for the selective preparation of 2-substituted 1,2,3-triazole isomers. In this context, we decided to develop an efficient flow synthesis for the preparation of various 2-aryl-1,2,3-triazoles. Our strategy involves a three-step synthesis under continuous-flow conditions that starts from the diazotization of anilines and subsequent reaction with malononitrile, followed by nucleophilic addition of amines, and finally employs a catalytic copper(II) cyclization. Potential safety hazards associated with the formation of reactive diazonium species have been addressed by inline quenching. The use of flow equipment allows reliable scale up processes with precise control of the reaction conditions. Synthesis of 2-substituted 1,2,3-triazoles has been achieved in good yields with excellent selectivities, thus providing a wide range of 1,2,3-triazoles.http://onlinelibrary.wiley.com/wol1/doi/10.1002/chem.201402074/full
http://onlinelibrary.wiley.com/store/10.1002/chem.201402074/asset/supinfo/chem_201402074_sm_miscellaneous_information.pdf?v=1&s=77c885224607254b0d594d6cd190e655dd4ac7ee

1H/13c NMR OF 1a









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10 Best Regional Foods you must Try in Mumbai!

1. The Street Food

From Paav Bhaji, Vada Paav, potato and onion Bhajias, Bombay sandwiches, street-sideDosas, Patti Samosas, Pani Puri, Sev Puri, Dahi Puri, Ragda Pattis, boiled Channa Chaat,Kala Khatta, raw mango slices and berries in Chinese Bhel Indian-style pizzas heaped with cheese to fresh fruit accompanied by real dairy cream that is rare to find in most places. This is a gastronomes delight. As layers of flavours, textures, colours create dishes that pop in your mouth and hardly impact your pocket, it maybe fun to play a guessing game of what came from where and how it may have transformed here.
Where – In South Mumbai, Girgaum Chowpatty snack shops, Bachelors for shakes, Indian style pizzas and sandwiches, and Homji Street Khao Galli (Fort) offer a spectrum of street food. Cannon (near CST) and Sardar (Tardeo) are famous for Pao Bhaji, Gurukrupa (Sion) for Samosa Ragda and Haj Ali Juice Centre for fresh juices, fruit cream, sandwiches and Indian style pizzas.

2. A Konkani Coastal Meal

The Konkan coast starts from Mumbai and goes on till Goa. Malvani cuisine is marked by the use of garam masala and red chilli. On the other hand, Gomantak cuisine is the coastal cuisine of areas in and around Goa and is marked by the generous use of fresh coconut and kokum. In most Mumbai restaurants, you’ll find a mix of Malvani and Gomatak cuisines. The curries here are tangy, coconut-y, fiery with spice and red chilli and accompanied by rice as the primary starch. Eat the catch of the day in a coconut-y curry poured over a heap of steaming white rice or mop them up with the variety of breads unique to this coast.

Where – Satkar (near Goregaon station) for Malvani, Highway Gomantak (on the Western Express Highway, Bandra East) and Goa House (Juhu), Singhudurg and Pradeep Gomatak (Fort).

3. A Typical Vegetarian Maharashtrian Meal

The star attractions that really pull crowds are snacks like Thaali Peeth (a sort of a multigrain pancake or flatbread), Kandha Pohe (flattened rice snack), Sabudana Vada(sago and potato fritter flecked with roasted peanuts), Misal Paav (a fiery curry made of pulses and fried nothings served with bun), Kothimbir Vadi (coriander leaf and gram flour fritters) etc. Aamras (fresh mango puree) when in season and Kharwas (a jelly like milky pudding made from the milk of a cow that has just given birth) round off the meal perfectly.
Where: Aaswad (opposite Sena Bhavan in Dadar) and Prakash (Dadar) though Vinay Health Home (Charni Road) comes highly recommended as well.

4. A South Indian Meal

The saga of Udupi cuisine began in this city when Rama Nayak arrived from Karnataka, in the 1940s. In Matunga, the area where a lot of South Indians lived, he set up his establishment near the King Circle railway station, and started cooking and serving authentic Udupi food on plantain leaves. This was Mumbai’s humble initiation into the idli-dosai menu. Soon Rama Nayak quadrupled his outlets into restaurants that are still known for great, uncompromising South Indian food in the city. Meanwhile, many other similar stories resulted in Udupi and Udupi-esque restaurants that cropped up all over the city, to be the primary dining room for the hungry working class of Mumbai.

Where: Most Udupi style restaurants have gotten Mumbaified in their offerings but there still are a few in Matunga like Ramanayaks Udupi (the thaali is what this place is most famous for), Udupi Idli House (absolutely fantastic range of idlis, chutneys and unlimitedsambhar), Café Madras (recommend almost everything here but the Podi Upma and Ragi Dosa are favourites), Ramashray (great idlis and dosas) and Manis Lunch Home (known for the thaalis).

5. Bori Mohalla Food Trail

It is said that Bohris are a Muslim business community who came from Gujarat and made great inroads into trade and commerce. The Muslim eat street of Mumbai, offers a cuisine distinct from other Mughal/Muslim cuisines of the country. While Mohammed Ali Road is famous for the food it offers for Iftar during Ramzan, Bohri Mohallah is the hidden gem of Mumbai that comes alive at dusk everyday, just as the evening prayers are being said at the Saifee mosque near by. In these gallis you will discover unique dishes of the Memon and Dawoodi Bohra inspired from regions as diverse as Surat, Delhi, Lucknow to United Kingdom, Malaysia, Iran, China and Yemen. Every kind of meat imaginable is on offer, cooked in myriad ways, served up as kebabs or in rich gravies. Breads range from naan to khamiri to fried paranthas and the murtabak like Baida Roti.

Where: Savoury – Sarvii Valibhai Payawal, Surti 12 Handi (Handi), Noor Mohamadi Hotel (Chicken Sanju Baba, the recipe for which was allegedly given to the hotel by Sanjay Dutt), Indian Hotel (kebabs and rolls), Mohammed Kareem Chana Masale Wala (Channa Masala).

6. An Irani Cafe for a Parsi Meal

Irani cafes (Iranis were the second batch of Zoroastrians to come to India from Persia) today offer simple menus with signature Parsi dishes including Salli Boti (a fantastic dish of melting mutton in a beautifully caramalised gravy, topped with crunchy fried potato straws), Mutton Dhansak (meat cooked in a creamy gravy of lentils and spices), Kheema Ghotala (curried minced mutton with an egg scrambled in, served with paav for breakfast) all to be washed down with the syrupy raspberry soda.

Where: Kyani (near Metro cinema) and Yazdani Bakery, Ideal Corner, Jimmy Boy (try their new Parsi Wedding feast), Military Cafe (all in Fort), Britannia (personally, I am of the opinion that the Berry Pulav is hyped but it certainly has great appeal and the berries themselves are a lovely tart-sweet payoff). In the suburbs, I would highly recommend theSalli Boti at Ashmit’s Snack Shack (Bandra, Pali Junction).

7. A Mangalorean Meal

The food along the west coast of India is a continuum of gradually  transforming flavours. As you reach Mangalore things start to get more meaty. The seafood and meat gravies including Ghassi (the most famous gravy of this region) are served up with the silky gossamer like Neer Dosa (thin rice pancakes). The coconut laden Sukkapreparations of mutton, squid or clams make for another brilliant combination with the soft Neer Dosas. Chicken Roti, another specialty of Mangalore is an intriguing dish of chicken curry with a roasted coconut gravy, served over crisp rice cracker ‘Kori Roti‘ that softens into a dosa on soaking up the chicken gravy.

Where: Apoorva (Fort) and Pratap Lunch Home (Fort) offer fantastic home-style food while Trishna (Fort) and Mahesh (Fort and Juhu) are more famous high end ones; great if you want to try crabs, jumbo prawns, lobster and pomfret in a tandoori masala or International sauces.

8. A Modern American/International Meal

An experience of Mumbai food would be incomplete without including the modern American/Continental, trendy, upmarket but just about affordable restaurants that have cropped up all over the city. A trend spearheaded by the enduring Indigo Restaurant and Deli which has become an institution in itself, these restaurants are rapidly increasing in number, available now in almost every mall as well as peppered around major office areas.

Where: Indigo Deli branches around the city, Indigo Restaurant (Colaba) broke new ground a decade ago in offering five star quality contemporary international food at relatively affordable prices in restaurants around the city.

9. Mumbai’s Old School Bars

While Mumbai, like other Indian cities has its share of international food to offer, your experience would be incomplete without a mention of its age old bars that attract tourists and city dwellers as much or maybe more for their ambiance and location as for the food. The food is a mix of ‘continental’ (Indianised grills, steaks, burgers, sandwiches, pastas) with the essential North Indian and Chinese thrown in for good measure. The colonial Parsi cafe meets old school 80’s pub meets dingy, overcrowded street-side restaurant ambiance of the ones in South Mumbai makes these almost into a right of passage for city new comers and college students.

Where: Leopold, Café Mondegar and Café Churchill all flank the Taj Mahal Hotel in Colaba. Totos Garage and Janata Bar are both in Bandra.

10. Regional Bests

If you want to try seriously authentic versions of cuisines from parts of the country you have never been to before, the city does offer a few restaurants that just about manage to escape Mumbaification.
Where: Head to Bhojohori Manna (Oshiwara) for superlative home-style Bengali food, Punjab Grill (Juhu or Phoenix Mills) for fantastically authentic Punjabi fare. Soam (Girgaum) and Hiralal Kashidas (Girgaon) make fantastic Gujarati Undhiyo when the season is right. Deluxe (Fort) and Just Kerala (Andheri East) are known for their non-vegetarian Kerala meal, Chetna (Fort) for its Rajasthani thali and Maharaja Bhog (Goregaon, Inorbit Mall) for a Gujarati and Rajasthani melange.






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